[ CAS No. 24391-41-1 ] {[proInfo.proName]}

Name: 24391-41-1|4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile|95%
Brand: Ambeed
SKU: A180745
Rating: 91 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 24391-41-1

Structure of 24391-41-1 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 24391-41-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 24391-41-1 ]

SDS Specification

Alternatived Products of [ 24391-41-1 ]

Product Details of [ 24391-41-1 ]

CAS No. :	24391-41-1	MDL No. :	MFCD12406095
Formula :	C₇H₃ClN₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NEWCOPCSNFUQQY-UHFFFAOYSA-N
M.W :	178.58	Pubchem ID :	22484542
Synonyms :

Calculated chemistry of [ 24391-41-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.61
TPSA :	65.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.26
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	1.28

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	0.804 mg/ml ; 0.0045 mol/l
Class :	Soluble
Log S (Ali) :	-2.31
Solubility :	0.866 mg/ml ; 0.00485 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.24
Solubility :	0.103 mg/ml ; 0.000577 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 24391-41-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 24391-41-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 24391-41-1 ]
Downstream synthetic route of [ 24391-41-1 ]

[ 24391-41-1 ] Synthesis Path-Upstream 1~6

1
[ 908287-23-0 ]
[ 24391-41-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With thionyl chloride In dichloromethane at 20℃;	To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (865 mg, 4.40 mmol, 1.0 eq) in DCM (20 mL), thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq) was added and the resulting mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo. The residue was suspended in water (60 mL) and saturated aqueous NaHC0₃ was added to adjust the pH to 4. The solid was collected by filtration, rinsed with water followed by ethyl acetate to afford the first batch of product. The filtrate was then extracted with ethyl acetate (50 mL x 3). The combined organic layer was washed with brine, dried over Na₂S0₄ and filtered. The filtrate was concentrated in vacuo and the residue was combined with the above -obtained solid. The crude product was then re -crystallized in ethyl acetate/hexanes (1 : 1) and dried in vacuo to afford 4-chloro-7H-pyrrolo[2,3- d]pyrimidine-5-carbonitrile (763 mg, 97percent yield). ESI-MS m/z: 178.8 [M+H]⁺, 176.8 [M-H]\
89.4%	With thionyl chloride In dichloromethane at 25 - 45℃;	Step 3: A suspension of C19 in DCM was treated drop-wise with thionyl chloride (10.38 g, 87 mmol, 10 eq.) and stirred at 25³C. After 5 hr. an additional 2 mL of SOCI₂ was added, and the reaction mixture was stirred overnight at 25^SC. The reaction mixture was then heated at 45⁰C for 1 hr., cooled to 25^SC, and concentrated. The resultant residue was treated with ethyl acetate, water and saturated sodium bicarbonate. The precipitate that formed in the separatory funnel was filtered. The filtrate was then extracted with ethyl acetate, and the combined organics were washed with brine, dried over Na₂SO₄, filtered, and concentrated to provide 0.5 g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (C20). The isolated precipitate (1.02 g) was stirred with aqueous ammonium chloride and ethyl acetate, the organic phase was collected, and the aqueous layer was extracted with ethyl acetate. The combined organics were concentrated to provide an additional 0.89 g of C20. Yield (total): 1.39 g, 89.4percent). ¹H NMR (DMSOd₆) δ: 13.70 (br s, 1 H), 8.78 (s, 1 H), 8.70 (s, 1 H) ppm.
77%	With thionyl chloride In dichloromethane at 20 - 40℃; for 22 h;	Synthesis of Compound 16.4 To a solution of compound 16.3 (3 g, 15 mmol) in DCM (60 ml) was added SOCl₂(11 ml, 153 mmol) at RT. After 5 hr, SOCl₂(5 ml) was added to the reaction. After 16 hr, the reaction was heated (40° C.) for 1 hr. The solvent was removed in vacuo. The residue was dissolved (EtOAc), washed (NaHCO₃sat.), dried (Na₂SO₄) and evaporated to afford compound 16.4 (2.1 g, 77percent) as an off-white solid. ¹H-NMR (500 MHz, DMSO-d6) δ 13.64 (bs, 1H), 8.76 (s, 1H), 8.67 (s, 1H). MS m/z 179 [M+1]⁺.

Reference： [1] Patent: WO2013/12915, 2013, A1, . Location in patent: Paragraph 00942
[2] Patent: WO2008/12635, 2008, A2, . Location in patent: Page/Page column 83
[3] Patent: US2009/5359, 2009, A1, . Location in patent: Page/Page column 25
[4] Patent: WO2011/146882, 2011, A1, . Location in patent: Page/Page column 110-111
[5] Patent: US2012/122838, 2012, A1, . Location in patent: Page/Page column 81-82

2
[ 22276-95-5 ]
[ 19158-51-1 ]
[ 24391-41-1 ]

Reference： [1] Patent: WO2012/80735, 2012, A1, . Location in patent: Page/Page column 12; 44

3
[ 22276-95-5 ]
[ 5285-74-5 ]
[ 24391-41-1 ]

Reference： [1] Patent: US6395733, 2002, B1,

4
[ 123148-78-7 ]
[ 2179-92-2 ]
[ 24391-41-1 ]

Reference： [1] Patent: WO2010/15637, 2010, A1, . Location in patent: Page/Page column 96

5
[ 3680-69-1 ]
[ 24391-41-1 ]

Reference： [1] Patent: WO2011/146882, 2011, A1,
[2] Patent: US2012/122838, 2012, A1,
[3] Patent: WO2012/80735, 2012, A1,
[4] Patent: WO2013/12915, 2013, A1,
[5] Patent: WO2010/15637, 2010, A1,

6
[ 22276-95-5 ]
[ 24391-41-1 ]

Reference： [1] Patent: WO2011/146882, 2011, A1,
[2] Patent: US2012/122838, 2012, A1,
[3] Patent: WO2013/12915, 2013, A1,

[ 24391-41-1 ] Synthesis Path-Downstream 1~48

1
[ 60374-77-8 ]
[ 24391-41-1 ]
[ 141232-11-3 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

2
[ 24391-41-1 ]
[ 53872-91-6 ]
[ 141232-13-5 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

3
[ 24391-41-1 ]
[ 53872-91-6 ]
[ 141232-12-4 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

4
[ 24391-41-1 ]
[ 13035-61-5 ]
[ 57071-52-0 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

7
[ 908287-23-0 ]
[ 24391-41-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With thionyl chloride; In dichloromethane; at 20℃;	To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (865 mg, 4.40 mmol, 1.0 eq) in DCM (20 mL), thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq) was added and the resulting mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo. The residue was suspended in water (60 mL) and saturated aqueous NaHC03 was added to adjust the pH to 4. The solid was collected by filtration, rinsed with water followed by ethyl acetate to afford the first batch of product. The filtrate was then extracted with ethyl acetate (50 mL x 3). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was combined with the above -obtained solid. The crude product was then re -crystallized in ethyl acetate/hexanes (1 : 1) and dried in vacuo to afford 4-chloro-7H-pyrrolo[2,3- d]pyrimidine-5-carbonitrile (763 mg, 97% yield). ESI-MS m/z: 178.8 [M+H]+, 176.8 [M-H]
89.4%	With thionyl chloride; In dichloromethane; at 25 - 45℃;	Step 3: A suspension of C19 in DCM was treated drop-wise with thionyl chloride (10.38 g, 87 mmol, 10 eq.) and stirred at 253C. After 5 hr. an additional 2 mL of SOCI2 was added, and the reaction mixture was stirred overnight at 25SC. The reaction mixture was then heated at 450C for 1 hr., cooled to 25SC, and concentrated. The resultant residue was treated with ethyl acetate, water and saturated sodium bicarbonate. The precipitate that formed in the separatory funnel was filtered. The filtrate was then extracted with ethyl acetate, and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated to provide 0.5 g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (C20). The isolated precipitate (1.02 g) was stirred with aqueous ammonium chloride and ethyl acetate, the organic phase was collected, and the aqueous layer was extracted with ethyl acetate. The combined organics were concentrated to provide an additional 0.89 g of C20. Yield (total): 1.39 g, 89.4%). 1H NMR (DMSOd6) delta: 13.70 (br s, 1 H), 8.78 (s, 1 H), 8.70 (s, 1 H) ppm.
77%	With thionyl chloride; In dichloromethane; at 20 - 40℃; for 22h;	Synthesis of Compound 16.4 To a solution of compound 16.3 (3 g, 15 mmol) in DCM (60 ml) was added SOCl2 (11 ml, 153 mmol) at RT. After 5 hr, SOCl2 (5 ml) was added to the reaction. After 16 hr, the reaction was heated (40 C.) for 1 hr. The solvent was removed in vacuo. The residue was dissolved (EtOAc), washed (NaHCO3 sat.), dried (Na2SO4) and evaporated to afford compound 16.4 (2.1 g, 77%) as an off-white solid. 1H-NMR (500 MHz, DMSO-d6) delta 13.64 (bs, 1H), 8.76 (s, 1H), 8.67 (s, 1H). MS m/z 179 [M+1]+.

		To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (E-4) (865 mg,4.40 mmol, 1.0 eq) in DCM (20 mL), thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq) is added and the resulting mixture is stirred at RT overnight. The reaction mixture is concentrated in vacuo. The residue is suspended in water (60 mL) and saturated aqueous NaHC03 is added to adjust the pH to 4. The solid is collected by filtration, rinsed with water followed by ethyl acetate to afford a first portion of product. The filtrate is then extracted with ethyl acetate (50 mL x 3). The combined organic layers are washed with brine, dried over Na2S04 and filtered. The filtrate is concentrated in vacuo and the residue is combined with the first portion of product. The product is then re-crystallized in ethyl acetate/hexanes (1 :1) and dried in vacuo to afford the final product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (E-5) as a pale solid.
	With thionyl chloride; In dichloromethane; at 20℃;	To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (G-3) (865 mg, 4.40 mmol, 1.0 eq) in DCM (20 mL), thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq) is added and the resulting mixture is stirred at RT overnight. The reaction mixture is concentrated in vacuo. The residue is suspended in water (60 mL) and saturated aqueous NaHCO3 is added to adjust the pH to 4. The solid is collected by filtration, rinsed with water and followed by ethyl acetate to afford the first batch of product. The filtrate is extracted with ethyl acetate (3*50 mL). The combined organic layers are washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo and the residue is combined with the above-obtained solid. The product is re-crystallized in ethyl acetate/hexanes (v/v=1/1) and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (G-4).

Reference： [1]Patent: WO2013/12915,2013,A1 .Location in patent: Paragraph 00942
[2]Patent: WO2008/12635,2008,A2 .Location in patent: Page/Page column 83
[3]Patent: US2009/5359,2009,A1 .Location in patent: Page/Page column 25
[4]Patent: WO2011/146882,2011,A1 .Location in patent: Page/Page column 110-111
[5]Patent: US2012/122838,2012,A1 .Location in patent: Page/Page column 81-82

8
[ 24391-41-1 ]
[ 475469-15-9 ]
[ 1004991-84-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃; for 5h;	Step 4: A mixture of C20 (1.739 g, 9.7 mmol), C14 (2.106 g, 9.7 mmol) and DIIPEA(3.56 mL, 20.5 mmol) was heated for five hr. at 8O0C. The DMF was removed under reduced pressure, and the resultant residue was treated with water and ethyl acetate. The mixture was then extracted with ethyl acetate (7 x 25 mL), and the combined organic phases were washed with saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resultant residue (3.36) was treated with DCM/MeOH, preabsorbed on 6.6 g silica gel, and chromatographed on Biotage Flash 4OL column, eluting with 6% MeOH/0.6% cone. NH4OH/DCM. The fractions containing product were combined and concentrated to provide [^(delta-cyano^H-pyrrolo^^-dlpyrimidin^-yO-S-hydroxymethyl-pyrrolidin-S-yll-carbamic acid tert-butyl ester (C21) as an off-white solid. Yield: 2.092 g, 60%. TLC (8%MeOH/DCM) Rf: 0.29. HPLC tn = 4.121 min.

Reference： [1]Patent: WO2008/12635,2008,A2 .Location in patent: Page/Page column 83

9
[ 24391-41-1 ]
[ 606-58-6 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

10
[ 24391-41-1 ]
[ 141232-14-6 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

11
[ 24391-41-1 ]
[ 139209-27-1 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

12
[ 24391-41-1 ]
[ 139209-29-3 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

13
[ 24391-41-1 ]
[ 141232-16-8 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

14
[ 24391-41-1 ]
[ 18417-89-5 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 391 - 404

15
[ 110-89-4 ]
[ 24391-41-1 ]
4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		METHOD O 4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile To a stirred solution of <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (54 mg/0.3 mmol) (prepared by the method of Townsend, et. al., J. Am. Chem. Soc., 1969, 91, 2102) suspended in 3.0 mL tert-Butanol was added piperidine (59 muL/0.60 mmol). The resulting mixture was then heated at reflux for 2.5 h and after cooling to room temperature, was transferred to a separatory funnel and diluted with ether (20 mL). The solution was extracted 2*10 mL with 1N HCl, the combined aqueous layers were adjusted to pH 7 with 2 N potassium hydroxide (KOH) solution forming a precipitate which was collected by filtration, washed with water and dried under reduced pressure to give 29 mg (42%) of the title compound as a colorless solid. Mp 209-211 C.; 1H NMR (400 MHz) (acetone-d6)delta: 1.72-1.74 (m, 6H), 3.72-3.79 (m, 4H), 8.12 (s, 1H), 8.29 (s, 1H). LRMS: 228 (M+1).
29 mg (42%)	In tert-butyl alcohol;	METHOD X 4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine-5carbonitrile To a stirred solution of <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (54 mg/0.3 mmol) (prepared by the method of Townsend, et. al., J. Am. Chem. Soc., 1969, 91, 2102) suspended in 3.0 mL tert-Butanol was added piperidine (59 muL/0.60 mmol). The resulting mixture was then heated at reflux for 2.5 h and after cooling to room temperature, was transferred to a separatory funnel and diluted with ether (20 mL). The solution was extracted 2*10 mL with 1N HCl, the combined aqueous layers were adjusted to pH 7 with 2 N potassium hydroxide (KOH) solution forming a precipitate which was collected by filtration, washed with water and dried under reduced pressure to give 29 mg (42%) of the title compound as a colorless solid. Mp 209-211 C.; 1H NMR (400 MHz) (acetone-6) delta1.72-1.74 (m, 6H), 3.72-3.79 (m, 4H), 8.12 (s, 1H), 8.29 (s, 1H). LRMS: 228 (M+1).

Reference： [1]Patent: US6635762,2003,B1 .Location in patent: Page/Page column 28
[2]Patent: US2002/19526,2002,A1

16
[ 22276-95-5 ]
[ 5285-74-5 ]
[ 24391-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; methanol; dichloromethane;	EXAMPLE 59 (3-ethynyl-phenylamino)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl-carbonitrile To 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.31 g, 1.3 mmol) in dry THF (4 ml), cooled in a dry ice-acetone bath, was added dropwise n-butyllithium (1.3 ml, 3.3 mmol, 2.5 M In hexanes). The reaction mixture was stirred for 1 hour, then p-toluenesulphenyl cyanide (0.44 g, 2.4 mmol) suspended in dry THF (7 ml) was added. The solution was stirred for 18 hours at ambient temperature then diluted with aqueous ammonium chloride. The phases were separated and the organic phase washed with water and aqueous NaCl. The organic phase was dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (15 g, 40 mm mesh) using 3% methanol/methylene chloride to afford 4-chloro5-cyano-7H-pyrrolo[2,3-d]pyrimidine as a yellow solid (52 mg).

Reference： [1]Patent: US6395733,2002,B1

17
[ 24391-41-1 ]
[ 167484-18-6 ]
benzyl 1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,2-dihydro-1'H-spiro[indole-3,4'-piperidine]-1'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium dihydrogenphosphate; phosphoric acid; In dimethyl sulfoxide; at 80℃; for 12h;	A solution of <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (1.0 g, 5.6 mmol), benzyl 1 ,2-dihydro-1'H-spiro[indole-3,4'-piperidine]-1'-carboxylate (1.80 g, 5.6 mmol), phosphoric acid (0.11g, 1.1 mmol), and potassium dihydrogen phosphate (0.76 g, 5.6 mmol) in 3 mL of dimethyl sulfoxide has heated at 8O0C for 12 h. The mixture was poured into 25% sodium bicarbonate in water (by weight) and extracted 3x with ethyl acetate. The combined organics were dried over sodium sulfate. Chromatography on silica gel, eluting with 62-65% ethyl acetate / hexanes afforded 1.94 g (74%) of benzyl 1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin- 4-yl)-1 ,2-dihydrc-1Eta-spiro[indole-3,4'-piperidine]-r-carboxylate; TR 7.54 min (HPLC Conditions H).

Reference： [1]Patent: WO2006/90261,2006,A1 .Location in patent: Page/Page column 63
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3359 - 3363

18
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime [ No CAS ]
[ 24391-41-1 ]

Yield	Reaction Conditions	Operation in experiment
89.4%	With thionyl chloride; In dichloromethane; at 20 - 45℃;	A sample of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (diastereomeric mixture) (1.71 g, 8.7 mmol) was suspended in methylene chloride and thionyl chloride (10.38 g, 87 mmol, 10 eq) was added dropwise. After 5 h stirring at rt, another 2 mL of SOCI2 was added and the reaction was stirred overnight at rt. The reaction was heated at 450C for 1 hr, the mixture was cooled to rt and was evaporated to dryness in vacuo. The mixture was taken up in ethyl acetate, water and saturated sodium bicarbonate. The precipitate that formed in the seperatory funnel was filtered. The filtrate was extracted with ethyl acetate and the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to yield 0.5 g of the desired compound. The isolated precipitate (1.02 g) was stirred with aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were evaporated to give an additional 0.89 g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (Total yield is 1.39 g, 89.4%). 1H NMR (DMSOd6) delta 13.70 (br s, 1H), 8.78 (s, 1 H), 8.70 (s, 1H) ppm.

Reference： [1]Patent: WO2006/90261,2006,A1 .Location in patent: Page/Page column 51; 63

19
[ 67-56-1 ]
[ 201230-82-2 ]
[ 24391-41-1 ]
[ 1095822-75-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With N-ethyl-N,N-diisopropylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 100℃; under 5171.62 Torr; for 16h;	Synthesis of Compound 16.5. A solution of compound 16.4 (600 mg, 3.4 mol), DIPEA (0.8 ml, 4.4 mmol), and Pd(dppf)2Cl2 (27 mg, 0.04 mmol) in MeOH (12 ml) under CO (100 psi) was heated (100 C.) for 16 hr. The solvent was removed in vacuo, and the residue was triturated (EtOAc) to afford compound 16.5 (400 mg, 58%) as an off-white solid. 1H-NMR (500 MHz, DMSO-d6) delta 13.64 (bs, 1H), 9.06(s, 1H), 8.80 (s, 1H), 3.98 (s, 3H). MS m/z 203 [M+1]+.

Reference： [1]Patent: US2009/5359,2009,A1 .Location in patent: Page/Page column 25

20
[ 123148-78-7 ]
[ 2179-92-2 ]
[ 24391-41-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 45; 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile; Tributyltin cyanide (1.12 g, 3.57 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.412 g, 0.357 mmol) are dissolved in dichloroethane (15 ml.) and the resulting solution is heated at reflux for 30 min under nitrogen. Then intermediate 38.2 (0.5 g, 1.785 mmol) is added. The reaction mixture is heated at reflux for 24 h. Concentration followed by purification by flash chromatography (silica 100-200 mesh, hexane : ethyl acetate = 70: 30) gives 4-Chloro-7H- pyrrolo[2,3-d]pyrimidine-5-carbonitrile (example 45) as a pale-yellow solid. 1H NMR (400 MHz, DMSO-de): delta 13.69 (brs, 1 H)1 1 104 (brs, 1 H), 8.77 (s, 1 H), 8.68 (ss 1 H).

Reference： [1]Patent: WO2010/15637,2010,A1 .Location in patent: Page/Page column 96

21
(R)-N-((3-aminopyrrolidin-3-yl)methyl)-2,4-difluorobenzamide [ No CAS ]
[ 24391-41-1 ]
(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-2,4-difluorobenzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4615 - 4622

22
C₁₂H₁₆FN₃O [ No CAS ]
[ 24391-41-1 ]
(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-4-fluorobenzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4615 - 4622

23
[ 1004992-38-4 ]
[ 24391-41-1 ]
(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-4-chlorobenzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4615 - 4622

24
[ 22276-95-5 ]
[ 24391-41-1 ]

Reference： [1]Patent: WO2011/146882,2011,A1
[2]Patent: US2012/122838,2012,A1
[3]Patent: WO2013/12915,2013,A1

25
[ 3680-69-1 ]
[ 24391-41-1 ]

Reference： [1]Patent: WO2011/146882,2011,A1
[2]Patent: US2012/122838,2012,A1
[3]Patent: WO2012/80735,2012,A1
[4]Patent: WO2013/12915,2013,A1
[5]Patent: WO2010/15637,2010,A1

26
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde [ No CAS ]
[ 24391-41-1 ]

Reference： [1]Patent: WO2011/146882,2011,A1
[2]Patent: US2012/122838,2012,A1
[3]Patent: WO2013/12915,2013,A1

27
[ 24391-41-1 ]
[ 76513-69-4 ]
[ 1383343-48-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	4-cUoro-lH-pyn-olo[2,3-d]pyrimidine-5-carbonitrile D42 ( 60mg) and potassium carbonate ( 282mg, 2.04mmol) were dissolved in DMF ( 6ml), {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane ( 69mg, 0.41mmol) was added dropwise. The reaction mixture was stirred at R.T. for 16 hours. The reaction mixture was poured onto water (30ml), extracted with EtOAc (60ml). Organic layer was washed with water (3x20ml), brine (20ml), dried (Na2S04), filtered and concentrated in vacuo to obtain a yellow oil of desired product D43 in 105mg. LCMS [MH+] 308.9 (at) 1.83 min ( 5 min run)

Reference： [1]Patent: WO2012/80735,2012,A1 .Location in patent: Page/Page column 12; 45

28
[ 22276-95-5 ]
[ 19158-51-1 ]
[ 24391-41-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of anhydrous THF (40ml) containing 5-Bromo-4-chloro-7H-pyrrolo[2,3- JJpyrimidine D3 (lg) was added nBu-Li (2.5M, 5.2ml, 12.9mmol) dropwise at -78C under nitrogen. After this addition the resulting solution was stirred for 1 hour at -78C before adding 4-methylbenzenesulfonyl cyanide (935mg, 5.2mmol) and the resulting solution stirred for 1 hour at -78C and then allowed to warm up to room temperature ovemight. The reaction was quenched with a saturated NH4CI solution at 0C, extracted with EtOAc (100ml) and organic layer was washed with 5% NaHC03 solution, dried a2S04, filtered and concentrated in vacuo to afford a yellow solid. Purified by flash chromatography on silica gel eluting with Pet Eth EtOAc 1/2 to give the desired product D42 as a yellow solid in 350mg. LCMS [MH+] 179.0 (at) 1.17 min ( 5 minrun)

Reference： [1]Patent: WO2012/80735,2012,A1 .Location in patent: Page/Page column 12; 44

29
[ 24391-41-1 ]
[ 1383342-17-3 ]

Reference： [1]Patent: WO2012/80735,2012,A1

30
[ 24391-41-1 ]
[ 1383343-51-8 ]

Reference： [1]Patent: WO2012/80735,2012,A1

31
(1r,4r)-1-N,1-N-dimethylcyclohexane-1,4-diamine dihydrochloride [ No CAS ]
[ 24391-41-1 ]
[ 1534374-52-1 ]

Yield	Reaction Conditions	Operation in experiment
20.0 mg	With triethylamine; In tert-butyl alcohol; at 100℃;	To a solution of <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (100 mg, 0.56 mmol, 1.00 equiv) in t-BuOH (15 mL) was added trans -N,N-dimethylcyclohexane-l,4-diamine (360 mg, 1.67 mmol, 3.0 equiv) and Et3N (3 ml). The resulting solution was stirred overnight at 100C in an oil bath. The resulting mixture was concentrated under vacuum and the residue was purified by Flash-Prep-HPLC with the following conditions: Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, water with 0.05% NH4HC03 and CH3CN (8.0% CH3CN up to 65.0% in 14 min); Detector, 254/220nm. This resulted in 20.0 mg of 4-((-4- (dimethylamino)cyclohexyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile as white solid. LCMS: (ES, m/z): 285[M+H]+ 1H NMR-(300 MHz, CD3OD, ppm): delta 8.22 (1H, d), 7.81 (1H, s), 3.95-4.05 (1H, m), 2.30-2.40 (7H, m), 2.23-2.29 (2H, m), 1.95-2.05 (2H, m),1.30-1.50 (4H, m).

Reference： [1]Patent: WO2014/11911,2014,A2 .Location in patent: Paragraph 00275; 00276

32
[ 64-18-6 ]
[ 1228947-14-5 ]
[ 24391-41-1 ]
4-(trans-(4-morpholinocyclohexyl)oxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile*0.7(formic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		To a solution of trans-4-(morpholin-4-yl)cyclohexan-l-ol (520 mg, 2.81 mmol, 5.01 equiv) in tetrahydrofuran (10 mL) was added sodium hydride (360 mg, 9.00 mmol, 16.07 equiv, 60%)). The resulting solution was stirred for 0.5 h at 0C. Then 4-chloro-7H-pyrrolo[2,3- d]pyrimidine-5-carbonitrile (100 mg, 0.56 mmol, 1.00 equiv) was added. The resulting solution was stirred for 16 h at 70C. The reaction was then quenched by the addition of 2 mL of water. The resulting mixture was concentrated under vacuum. The crude product (100 mg) was purified by Prep-HPLC with the following conditions: Column, Xbridge Prep CI 8 5um, 19* 150mm; mobile phase, water with 0.1% HCOOH and CH3CN (5.0% CH3CN up to 40.0% in 12 min, up to 92.0% in 2 min, down to 5.0% in 2 min); Detector, 220/254nm. This resulted in 70.2 mg (34%) of 4-(tra/75-(4-morpholinocyclohexyl)oxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile as a white solid. LC-MS: (ES,m z): 328[M-0.7HCOOH+H] + 1H NMR (300 MHz, DMSO, ppm): 51.54-1.88 (m, 4H), 2.13-2.14 (m, 2H), 2.16-2.23 (m, 2H), 2.27-2.29 (m, 1H), 2.45-2.55 (m, 4H), 3.46-3.55 (m, 4H), 5.14-5.21 (m, 1H) , 8.09 (s, 0.7H), 8.27 (s, 1H), 8.50 (s, 1H), 12.97 (brs, 0.9H).

Reference： [1]Patent: WO2014/11911,2014,A2 .Location in patent: Paragraph 00279; 00280

33
[ 24391-41-1 ]
trans-4-(dimethylamino)cyclohexan-1-ol [ No CAS ]
[ 1534374-53-2 ]

Yield	Reaction Conditions	Operation in experiment
19%		To a solution of 4-(dimethylamino)cyclohexan-l-ol (320 mg, 2.23 mmol, 3.99 equiv) in tetrahydrofuran (10 mL) was added sodium hydride (360 mg, 9.00 mmol, 26.79 equiv) at 0C. The resulting solution was stirred for 30 min at 0C. Then 4-chloro-7H-pyrrolo[2,3- d]pyrimidine-5-carbonitrile (100 mg, 0.56 mmol, 1.00 equiv) was added. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux. The reaction was then quenched by the addition of 2 mL of water. The resulting mixture was concentrated under vacuum. The crude product (80 mg) was purified by Prep-HPLC with the following conditions: Column, Xbridge Prep C 18 5um, 19x150mm; mobile phase, water with 50mL HCOOH and CH3CN (5.0% CH3CN up to 42.0% in 10 min, up to 95.0% in 2 min, down to 5.0%) in 2 min); Detector, 220/254nm. 30.2 mg product was obtained. This resulted in 30.2 mg (19%) of 4-[[4-(dimethylamino)cyclohexyl]oxy]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile as a brown solid. LC-MS:(ES,m/z): 286 [M+H]+ 1H NMR (300 MHz, DMSO, ppm): 51.18-1.55 (m, 4H), 1.86-1.89 (d, 2H), 2.13-2.17 (d, 2H), 2.17 (s, 6H), 2.39 (m, 1H),5.15-5.20 (m, 1H), 8.22- 8.26 (m, 2H), 8.43 (s, 1H).

Reference： [1]Patent: WO2014/11911,2014,A2 .Location in patent: Paragraph 00277; 00278

34
[ 1548339-64-5 ]
[ 24391-41-1 ]
[ 1548333-77-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In butan-1-ol; at 130℃; for 2h;	Step 2-3 (5)-4-(2-(5-chloro-3-(2,2-difluoroethyl)-4-oxo-3,4-dihydropyrrolo[l ,2-f] [l,2,4]triazin-2-yl)azetidin-l-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (59) Compound 59 A mixture of 2c (0.59 mmol), <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (105 mg, 0.59 mmol) and TEA (0.41 mL, 2.95 mmol) in n-BuOH (9 mL) was heated at 130 C for 2 hours. After concentration, the residue was washed with water and dried, then purified by preparative TLC and Compound 59 as a pale yellow solid was obtained (160mg, yield: 63%). MS (m/z): 431.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 12.94 (s, 1H), 8.32 (m, 2H), 7.67 (s, 1H), 6.67 (s, 1H), 6.45 (t, / = 55.2 Hz, 1H), 5.92-5.82 (m, 1H), 4.80-4.54 (m, 2H)? 4.52-4.26 (m, 2H), 3.06-2.96 (m, 1H), 2.78-2.66 (m, 1H)
63%	With triethylamine; In butan-1-ol; at 130℃; for 2h;	A mixture of 2c (0.59 mmol), <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (105 mg, 0.59 mmol) and TEA (0.41 mL, 2.95 mmol) in n-BuOH (9 mL) was heated at 130 C for 2 hours. After concentration, the residue was washed with water and dried, then purified by preparative TLC and Compound 59 as a pale yellow solid was obtained (160mg, yield: 63%). MS (m/z): 431.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 12.94 (s, 1H), 8.32 (m, 2H), 7.67 (s, 1H), 6.67 (s, 1H), 6.45 (t, J = 55.2 Hz, 1H), 5.87 (m, 1H), 4.67 (m, 2H), 4.52 - 4.26 (m, 2H), 3.01 (m, 1H), 2.72 (m, 1H).
63%	With triethylamine; In butan-1-ol; at 130℃; for 2h;	A mixture of 2c (0.59 mmol), <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (105 mg, 0.59 mmol) and TEA (0.41 mL, 2.95 mmol) in n-BuOH (9 mL) was heated at 130 C for 2 hours. After concentration, the residue was washed with water and dried, then purified by preparative TLC and Compound 59 as a pale yellow solid was obtained (160mg, yield: 63%). MS (m/z): 431.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta:12.94 (s, 1H), 8.32 (m, 2H), 7.67 (s, 1H), 6.67 (s, 1H), 6.45 (t, J = 55.2 Hz, 1H),5.92-5.82 (m, 1H), 4.80-4.54 (m, 2H),, 4.52-4.26 (m, 2H), 3.06-2.96 (m, 1H), 2.78-2.66 (m, 1H)

Reference： [1]Patent: WO2014/15675,2014,A1 .Location in patent: Page/Page column 74
[2]Patent: WO2014/15523,2014,A1 .Location in patent: Page/Page column 52; 53
[3]Patent: WO2014/15830,2014,A1 .Location in patent: Page/Page column 73; 74; 75

35
[ 1548341-37-2 ]
[ 24391-41-1 ]
[ 1548335-65-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine; In butan-1-ol; for 2h;Reflux;	A mixture of 13b (0.16 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine- 5-carbonitrile (28 mg, 0.16 mmol) and TEA (0.08 mL, 0.58 mmol) in n-BuOH (5 mL) was stirred at reflux for 2 hours. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/water to afford Compound 106 as a white solid (27 mg, yield: 62%). MS (m/z): 364.7 (M+H)+. 1HNMR (400 MHz, DMSO-d6) delta: 13.07 - 12.72 (m, 1H), 11.76 (s, 1H), 8.30 (s, 1H), 8.13 (s, 1H), 6.77 (m, 1H), 6.31 - 6.09 (m, 1H), 5.1 1 (m, 1H), 4.28 (m, 1H), 3.94 (m, 1H), 2.40 - 2.30 (m, 1H), 2.18 - 2.02 (m, 3H).
27 mg	With triethylamine; In butan-1-ol; for 2h;Reflux;	Step 13-3 (5)-4-(2-(7-fiuoro-4-oxo-3,4-dihydropyrrolo[l,2-f][l,2,4]triazin-2-yl) pyrrolidin- 1 -yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (106) Compound 106 A mixture of 13b (0.16 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine- 5-carbonitrile (28 mg, 0.16 mmol) and TEA (0.08 mL, 0.58 mmol) in n-BuOH (5 mL) was stirred at reflux for 2 hours. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/water to afford Compound 106 as a white solid (27 mg, yield: 62%). MS (m/z): 364.7 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 13.07-12.72 (m, 1H), 11.76 (s, 1H), 8.30 (s, 1H), 8.13 (s, 1H), 6.81-6.73 (m, 1H), 6.31-6.09 (m, 1H), 5.15-5.07 (m, 1H), 4.32-4.24 (m, 1H), 3.96-3.92 (m, 1H), 2.40-2.30 (m, 1H), 2.18-2.02 (m, 3H).

Reference： [1]Patent: WO2014/15523,2014,A1 .Location in patent: Page/Page column 93
[2]Patent: WO2014/15675,2014,A1 .Location in patent: Page/Page column 120

36
[ 1548341-44-1 ]
[ 24391-41-1 ]
[ 1548335-67-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	With triethylamine; In butan-1-ol; for 2h;Reflux;	Step 14-3 (5)-4-(2-(7-fluoro-3 -isobutyl-4-oxo-3 ,4-dihydropyrrolo [ 1 ,2-f] [ 1 ,2,4]triazin -2-yl)pyrrolidin- 1 -yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (107) Compound 107 A mixture of 14b (0.132 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (24 mg, 0.132 mmol) and TEA (0.09 mL, 0.66 mmol) in n-BuOH (10 mL) was heated at reflux for 2 hours. The reaction mixture was concentrated purified by flash column chromatography eluting with MeOH/water to afford compound 107 as a slight yellow solid (17 mg, yield: 31%). MS (m/z): 420.7 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) delta: 8.29 (s, 1H), 8.03 (s, 1H), 6.77 (t, / = 5.1 Hz, 1H), 6.16 (t, / = 4.0 Hz, 1H), 5.55-5.45 (m, 1H), 4.30-4.22 (m, 1H), 4.18-4.05 (m, 2H), 3.71-3.67 (m, 1H), 2.37-2.01 (m, 5H), 1.00 (d, / = 6.6 Hz, 3H), 0.93 (d, / = 6.5 Hz, 3H).
31%	With triethylamine; In butan-1-ol; for 2h;Reflux;	A mixture of 14b (0.132 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (24 mg, 0.132 mmol) and TEA (0.09 mL, 0.66 mmol) in n-BuOH (10 mL) was heated at reflux for 2 hours. The reaction mixture was concentrated purified by flash column chromatography eluting with MeOH/water to afford compound 107 as a slight yellow solid (17 mg, yield: 31%). MS (m/z): 420.7 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) delta: 8.29 (s, 1H), 8.03 (s, 1H), 6.77 (t, J= 5.1 Hz, 1H), 6.16 (t, J= 4.0 Hz, 1H), 5.50 (m, 1H), 4.26 (m, 1H), 4.15 - 4.08 (m, 2H), 3.69 (m, 1H), 2.37 - 2.01 (m, 5H), 1.00 (d, J= 6.6 Hz, 3H), 0.93 (d, J= 6.5 Hz, 3H).
31%	With triethylamine; In butan-1-ol; for 2h;Reflux;	A mixture of 14b (0.132 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (24 mg, 0.132 mmol) and TEA (0.09 mL, 0.66 mmol) in n-BuOH (10 mL) was heated at reflux for 2 hours. The reaction mixture was concentrated purified by flash column chromatography eluting with MeOH/water to afford compound 107 as a slight yellow solid (17 mg, yield: 31%). MS (m/z): 420.7 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) delta: 8.29 (s, 1H), 8.03 (s, 1H), 6.77 (t, J= 5.1 Hz, 1H), 6.16 (t, J= 4.0 Hz, 1H), 5.55-5.45 (m, 1H), 4.30-4.22 (m, 1H), 4.18-4.05 (m, 2H), 3.71-3.67 (m, 1H), 2.37-2.01 (m, 5H), 1.00 (d, J= 6.6 Hz, 3H), 0.93 (d, J= 6.5 Hz, 3H).

Reference： [1]Patent: WO2014/15675,2014,A1 .Location in patent: Page/Page column 122
[2]Patent: WO2014/15523,2014,A1 .Location in patent: Page/Page column 95
[3]Patent: WO2014/15830,2014,A1 .Location in patent: Page/Page column 119; 120; 121

37
[ 1548339-56-5 ]
[ 24391-41-1 ]
[ 1548331-43-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine; In butan-1-ol; for 1.5h;Reflux;	Step 1 -5 (S)-4-(2-(4-oxo-3-phenyl-3,4-dihydropyrrolo[ 1 ,2-fJ [ 1 ,2,4]triazin-2-yl) pyrrolidin- 1 -yl)-7H- rrolo [2,3 -d]pyrimidine-5 -carbonitrile (Compound 1 ) Compound 1 A mixture of le (30 mg, 0.095 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (22 mg, 0.128 mmol) and TEA (0.05 ml, 0.360 mmol) in n-BuOH (3 mL) was stirred at reflux for 1.5 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/DCM to afford Compound 1 as a white solid (29 mg, yield: 64%). MS (m/z): 422.6 (M+H)+. 1H NMR (400 MHz, DMSO-de) delta: 12.81 (s, 1H), 8.27-8.26 (m, 2H), 7.72-7.68 (m, 1H) , 7.64-7.41 (m, 5H), 6.88 (dd, / = 4.3, 1.7 Hz, 1H), 6.47 (dd, / = 4.3, 2.7 Hz, 1H), 4.72-4.65 (m, 1H), 4.12-4.06 (m, 1H), 3.96-3.89 (m, 1H), 2.35-2.15 (m, 2H) 2.06-1.83 (m, 2H).
64%	With triethylamine; In butan-1-ol; for 1.5h;Reflux;	A mixture of 1e (30 mg, 0.095 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (22 mg, 0.128 mmol) and TEA (0.05 ml, 0.360 mmol) in n-BuOH (3 mL) was stirred at reflux for 1.5 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/DCM to afford Compound 1 as a white solid (29 mg, yield: 64%). MS (m/z): 422.6 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 12.81 (s, 1H), 8.27-8.26 (m, 2H), 7.72-7.68 (m, 1H) , 7.64-7.41 (m, 5H), 6.88 (dd, J= 4.3, 1.7 Hz, 1H), 6.47 (dd, J = 4.3, 2.7 Hz, 1H), 4.72-4.65 (m, 1H), 4.12-4.06 (m, 1H), 3.96-3.89 (m, 1H), 2.35-2.15 (m, 2H) 2.06-1.83 (m, 2H).
	With triethylamine; In butan-1-ol; for 1.5h;Reflux;	A mixture of 1e (30 mg, 0.095 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (22 mg, 0.128 mmol) and TEA (0.05 ml, 0.360 mmol) in n-BuOH (3 mL) was stirred at reflux for 1.5 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/DCM to afford Compound 1 as a white solid (29 mg, yield: 64%). MS (m/z): 422.6 (M+H)+. 1H NMR (400 MHz, DMSO- d6) delta: 12.81 (s, 1H), 8.27 - 8.26 (m, 2H), 7.70 (m, 1H), 7.64 - 7.41 (m, 5H), 6.88 (dd, J = 4.3, 1.7 Hz, 1H), 6.47 (dd, J= 4.3, 2.7 Hz, 1H), 4.68 (m, 1H), 4.10 (m, 1H), 3.92 (m, 1H), 2.23 (m, 2H), 2.06 - 1.83 (m, 2H).

Reference： [1]Patent: WO2014/15675,2014,A1 .Location in patent: Page/Page column 47
[2]Patent: WO2014/15830,2014,A1 .Location in patent: Page/Page column 47; 49
[3]Patent: WO2014/15523,2014,A1 .Location in patent: Page/Page column 36; 38

38
cis-4-[1-(2-azetidin-1-ylethyl)-4-(4-fluoro-3-trifluoromethylphenyl)-1H-imidazol-2-yl]-3-fluoropiperidine [ No CAS ]
[ 24391-41-1 ]
4-{cis-4-[1-(2-azetidin-1-ylethyl)-4-(4-fluoro-3-trifluoromethylphenyl)-1H-imidazol-2-yl]-3-fluoropiperidin-1-yl}-7H-pyrrolo[2.3-d]pyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 50℃; for 36h;	A reaction mixture of <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (24.61 mg; 0.14 mmol; 1.02 eq.), cis-4-[1 -(2-azetidin-1 -yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1 H- imidazol-2-yl]-3-fluoro-piperidine (56.00 mg; 0.14 mmol; 1 .00 eq.), and ethyldiisopropylamine (22.70 mg; 0.18 mmol; 1 .30 eq.) in ACN (1 ml) was stirred at 50C for 36 hr. After cooling to rt, the precipate was collected by filtration to yield the title compound as a yellow solid. LC-MS (M+H = 557, obsd. = 557).

Reference： [1]Patent: WO2014/143612,2014,A1 .Location in patent: Page/Page column 68-69

39
C₁₀H₂₀N₂O₂ [ No CAS ]
[ 24391-41-1 ]
C₂₄H₂₇N₇O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4005 - 4010

40
C₁₀H₂₀N₂O₂ [ No CAS ]
[ 24391-41-1 ]
C₁₆H₂₀N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide;Reflux;	General procedure: To a mixture of ArCl (22.92 mmol) and piperidinederivative (27.5 mmol, 1.2 eq) in Water/DMSO (35 mL/35 mL) was added DIPEA(32.0 mL, 183 mmol, 8 eq). The resulting mixture was refluxed overnight andcooled to room temperature. The suspension was diluted with H2O (500ml) and neutralized by dropwise addition of concentrated aqueous HCl to pH 6.3.The solid was collected by filtration and washed with H2O. The solidwas then dissolved in 1M aqueous NaOH (200 ml) and filtered. The filtrate wasneutralized by dropwise addition of concentrated HCl to pH 6.7, resulting in abeige precipitation. The solid was collected by filtration and washed with H2O,ACN (2x) and Et2O. The obtained powder was suspended in ACN andfreeze-dried to afford the desired intermediate, which was used for the nextstep without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4005 - 4010

41
methyl 3-{4-[(dimethylamino)methyl]piperidine-4-amido}benzoate [ No CAS ]
[ 24391-41-1 ]
C₂₄H₂₇N₇O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 120℃; for 48h;	General procedure: Piperidinederivative (0.94 mmol, 1.0 eq), ArCl (2.35 mmol, 2.5eq.), N,N-diisopropylethylamine (1200 mg, 9.4 mmol, 10.0 eq) and i-PrOH (20 mL)were combined and heated at 120 C for 48 h. The solvent was removed undervacuum and the residue was purified by preparative HPLC to give the expected finalcompounds.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4005 - 4010

42
[ 24391-41-1 ]
[ 613660-87-0 ]
4-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7043 - 7066

43
[ 5292-43-3 ]
[ 24391-41-1 ]
tert-butyl 2-(4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		To a solution of <strong>[24391-41-1]4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (57a) (811 mg, 4.54 mmol) in DMF (10 mL) was added at room temperature, NaH (60% in mineral oil, 218 mg, 5.45 mmol) stirred for 5 mins followed by the addition of tert-butyl 2-bromoacetate (0.81 mL, 5.45 mmol). The reaction mixture was stirred for 2 h quenched with EtOAc (50 mL) and brine (75 mL). The organic layer was separated washed with water (50 mL), dried, filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography [silica gel (24 g), eluting with MeOH in CHCh 0 to 30%] to afford tert-butyl 2-(4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate (57b) (989 mg, 3.38 mmol, 74% yield) as an off-white solid; MR (300 MHz, VMSO-de) delta 8.86 (s, 1H), 8.71 (s, 1H), 5.18 (s, 2H), 1.42 (s, 9H); MS (ES+): 293.4 (M+l), 315.3 (M+Na); (ES-): 291.3 (M-l), 327.4 (M+Cl).

Reference： [1]Patent: WO2017/136395,2017,A1 .Location in patent: Page/Page column 125; 126

44
[ 24391-41-1 ]
2-(4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2017/136395,2017,A1

45
[ 1403942-66-4 ]
[ 24391-41-1 ]
[ 1548331-43-6 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4936 - 4948

46
[ 24391-41-1 ]
C₂₁H₂₂ClFN₄O₃ [ No CAS ]
[ 1548334-22-0 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4936 - 4948

47
[ 1548343-96-9 ]
[ 24391-41-1 ]
[ 1548332-62-2 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4936 - 4948

48
[ 24391-41-1 ]
tert-butyl (S)-2-(5-chloro-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-2-yl)pyrrolidine- 1-carboxylate [ No CAS ]
[ 1548332-49-5 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4936 - 4948

Recommend Products

Same Skeleton Products

Related Products

Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • An Alkane are Prepared from an Haloalkane • Blaise Reaction • Catalytic Hydrogenation • Chloroalkane Synthesis with SOCI2 • Complex Metal Hydride Reductions • Convert Haloalkanes into Alcohols by SN2 • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • DIBAL Attack Nitriles to Give Ketones • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Hydride Reductions • Ketone Synthesis from Nitriles • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Nitriles Hydrolyze to Carboxylic Acids • Preparation of Aldehydes and Ketones • Preparation of Amines • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Ritter Reaction • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Thorpe-Ziegler Reaction

Historical Records

Related Functional Groups of
[ 24391-41-1 ]

Chlorides

[ 1618-36-6 ]

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.89

[ 35808-68-5 ]

4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.76

[ 115093-90-8 ]

4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.76

[ 71149-52-5 ]

4-Chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.75

[ 123148-78-7 ]

4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.73

Nitriles

[ 53491-80-8 ]

1-Chloroisoquinoline-4-carbonitrile

Similarity: 0.62

[ 99586-66-0 ]

2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile

Similarity: 0.60

[ 3177-24-0 ]

2,4-Dichloropyrimidine-5-carbonitrile

Similarity: 0.59

[ 1231761-23-1 ]

1-Chloroisoquinoline-5-carbonitrile

Similarity: 0.59

[ 4414-89-5 ]

1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile

Similarity: 0.58

Related Parent Nucleus of
[ 24391-41-1 ]

Other Aromatic Heterocycles

[ 1618-36-6 ]

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.89

[ 35808-68-5 ]

4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.76

[ 115093-90-8 ]

4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.76

[ 71149-52-5 ]

4-Chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.75

[ 123148-78-7 ]

4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.73

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 24391-41-1 ] {[proInfo.proName]}

Quality Control of [ 24391-41-1 ]

Related Doc. of [ 24391-41-1 ]

Product Details of [ 24391-41-1 ]

Calculated chemistry of [ 24391-41-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 24391-41-1 ]

Application In Synthesis of [ 24391-41-1 ]

[ 24391-41-1 ] Synthesis Path-Upstream 1~6

[ 24391-41-1 ] Synthesis Path-Downstream 1~48

Technical Information

Related Functional Groups of [ 24391-41-1 ]

Chlorides

Nitriles

Related Parent Nucleus of [ 24391-41-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 24391-41-1 ]

Related Parent Nucleus of
[ 24391-41-1 ]