400777-00-6|tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate| Ambeed

Structure of 400777-00-6

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Quality Control of [ 400777-00-6 ] Purity: 98% SDS Specification

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Product Details of [ 400777-00-6 ]

CAS No. :	400777-00-6
Formula :	C₁₀H₁₂ClIN₂O₂
M.W :	354.57
SMILES Code :	O=C(OC(C)(C)C)NC1=C(I)C=C(Cl)N=C1
MDL No. :	MFCD11977418
InChI Key :	YCBOUHLCYYKTFG-UHFFFAOYSA-N
Pubchem ID :	53415320

Safety of [ 400777-00-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 400777-00-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	72.21
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.22 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.83
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.5
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.22
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.78
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.87

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.96
Solubility	0.0388 mg/ml ; 0.000109 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.77
Solubility	0.0601 mg/ml ; 0.000169 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.5
Solubility	0.0112 mg/ml ; 0.0000316 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.31 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.61

Application In Synthesis of [ 400777-00-6 ]

* 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.

Downstream synthetic route of [ 400777-00-6 ]

[ 400777-00-6 ] Synthesis Path-Downstream 1~35

1
[ 171178-45-3 ]
[ 400777-00-6 ]

Yield	Reaction Conditions	Operation in experiment
33%		Step b: tert-Butyl 6-chloro-4-iodopyridin-3-ylcarbamate To a solution of TMEDA (25.4 g, 219.3 mmol) in dry THF (300 mL) was added dropwise n-BuLi (87.7 mL, 219.3 mmol) at -78 C., the mixture was stirred for 0.5 h at this temperature. A solution of tert-butyl 6-chloropyridin-3-yl-carbamate (20 g, 87.7 mmol) in THF (170 mL) was added dropwise to the reaction mixture at -78 C. and the resulting mixture was continued to stir for 1 h at -78 C. Then a solution of I2 (26.7 g, 105.3 mmol) in dry THF (170 mL) was added dropwise at -78 C. After 1 h, the reaction was quenched with sat. aqueous NH4Cl (300 mL). The organic layer was separated and the aqueous phase was extracted with EtOAc (150 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield a residue that was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1) to give tert-butyl 6-chloro-4-iodopyridin-3-ylcarbamate (10.0 g, 33%). 1H-NMR (CDCl3, 400 MHz) delta 8.95 (s, 1H), 7.73 (s, 1H), 6.64 (br s, 1H), 1.53 (s, 9H).
32.3%		Step 2 To the solution of tert-butyl (6-chloropyridin-3-yl)carbamate (160 g, 0.7 mol) in 1 L of anhydrous THF was added n-BuLi (600 mL, 1.5 mol) at -78 C. under N2 atmosphere. After the addition was finished, the solution was stirred at -78 C. for 30 min, and the solution of I2 (177.68 g, 0.7 mol) in 800 mL of anhydrous THF was added. Then the solution was stirred at -78 C. for 4 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and purified by flash chromatography to afford 80 g of tert-butyl (6-chloro-4-iodopyridin-3-yl)carbamate as a yellow solid (32.3%).
32.3%		Step 2: (0190) To the solution of tert-butyl(6-chloropyridin-3-yl)carbamate (160 g, 0.7 mol) in 1 L of anhydrous THF was added n-BuLi (600 mL, 1.5 mol) at -78 C. under N2 atmosphere. After the addition was finished, the solution was stirred at -78 C. for 30 min, and the solution of I2 (177.68 g, 0.7 mol) in 800 mL of anhydrous THF was added. Then the solution was stirred at -78 C. for 4 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and purified by flash chromatography to afford 80 g of tert-butyl(6-chloro-4-iodopyridin-3-yl)carbamate as a yellow solid (32.3%).

32.3%		To the solution of tert-butyl (6-chloropyridin-3-yl)carbamate (160 g, 0.7 mol) in 1 L of anhydrous THF was added n-BuLi (600 mL, 1.5 mol) at -78 C. under N2atmosphere. After the addition was finished, the solution was stirred at -78 C. for 30 min, and the solution of I2(177.68 g, 0.7 mol) in 800 mL of anhydrous THF was added. Then the solution was stirred at -78 C. for 4 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and purified by flash chromatography to afford 80 g of tert-butyl (6-chloro-4-iodopyridin-3-yl)carbamate as a yellow solid (32.3%).
		Preparation 7 : (6-Chloro-4-iodopyridin-3-yl)carbamic acid tert-butyl ester The title compound was prepared according to the method described in US 2002/0022624 Al from the compound of Preparation 6. 5H(CDC13): 1.54 (9H, s), 6.62 (IH, s), 7.72 (IH, s), 8.93 (IH, s).
		Step B: tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamateteri-Butyllithium (1.3 M in heptanes, 1 11 mL, 144 mmol) was added dropwise to a solution of t-butyl (6-chloropyridin-3-yl)carbamate (15.0 g, 65.6 mmol) in anhydrous THF (300 mL) at -78 C over 30 min under 2 atmosphere. The resulting mixture was stirred at -78 C for 1 h, then at -10 C for 1 h. The reaction mixture was cooled to -78 C and a solution of I2 (36.6 g, 144 mmol) in anhydrous THF (100 mL) was added. The resulting mixture was warmed to ambient temperature and stirred for 18 h. Excess ?-butyllithium and I2 were quenched with saturated aqueous NH4C1 solution (150 mL) and saturated aqueous a2S203 solution (500 mL), respectively, and the resulting mixture was stirred for 30 min. The organic layer was separated and the aqueous layer was extracted with EtOAc (250 mL x 2). The combined organic layers were washed with brine (250 mL), dried over Na2S04 and concentrated. The residue was purified by column chromatography on silica gel (EtOAc:PE:Et3N = 2 : 98 : 1, then 2.5 : 97.5 : 1) to afford the title compound. MS: m/z = 355 (M + 1). XH NMR (400 MHz, CDC13) delta 8.93 (s, 1H), 7.72 (s, 1H), 6.64 (s, 1H), 1.53 (s, 9H).
2.59 g		Under argon gas atmosphere, to diethyl ether (120mL)solution of (6-chloropyridin-3-yl) carbamic acid tert- butyl (5.0 g) and N, N,N ', N'- tetramethyl ethane-1,2-diamine (7.7 g), at -78 n-butyl lithium solution (2.65mol / L tetrahydrofuran solution, 25mL) was addeddropwise. after stirring the mixture for 2 hours at -10 , diethyl ether (40mL) solution of iodine (11.4g) wasdropped at -78 , and the mixture was stirred one day at roomtemperature. To the reaction mixture, a saturated aqueous ammonium chloridesolution was added, and extracted with diethyl ether. The organic layer was washed with 10%aqueous solution of sodium pyrosulfite and saturated brine, dried overanhydrous magnesium sulfate, and evaporated under reduced pressure. Theresulting crude product was purified by silica gel column chromatography (eluting solvent: n- hexane / ethyl acetate = 100 / 0 ~60 / 40) to give the title compound (2.59 g).
2.59 g		To a solution of (6-chloropyridin-3-yl)carbamic acid tert-butyl ester(5.0 g) at -78 C and N, N, N ', N'-tetramethylethane-1,2-diamine (7.7 g) of diethyl ether (120 mL) after the drop of the solution was stirred at 10 C for 2 hours, iodine (11.4 g) was added dropwise at -78 C, of diethyl ether (40 mL) solution. The mixture was stirred at room temperature for one day. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and extracted with diethyl ether. The organic layer was washed with 10% aqueous sodium metabisulfite solution, after washing with saturated saline, and then dried over anhydrous magnesium sulfate, and distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (elution solvent; n-hexane-ethyl acetate) to give the title compound (2.59 g).
2.59 g		Reference Example 4 (0080) (6-Chloro-4-iodopyridin-3-yl)cathamic acid tert-butyl ester (0081) To a solution of (6-chloropyridin-3-yl)cathamic acid tert-butyl ester (5.0 g) and N,N,N?,N-tetramethylethane-1,2-diamine (7.7 g) in diethyl ether (120 mL) was added dropwise n-buthyllithium (2.65 mol/L n-hexane solution, 25 mL) at -78 C. under an argon gas atmosphere. After the mixture was stirred at -10 C. for 2 hours, a solution of iodine (11.4 g) in diethyl ether (40 mL) was added dropwise at -78 C. The resulting mixture was stirred at room temperature for 1 day. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with 10% aqueous sodium pyrosulfite and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (2.59 g).

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3405 - 3408.
[3]Patent: US2009/253736,2009,A1 .Location in patent: Page/Page column 28-29.
[4]Patent: US8426450,2013,B1 .Location in patent: Page/Page column 28; 29.
[5]Patent: US9403772,2016,B2 .Location in patent: Page/Page column 33.
[6]Patent: JP2015/17121,2015,A .Location in patent: Paragraph 0164; 0166.
[7]Inorganic Chemistry,2017,vol. 56,p. 8381 - 8389.
[8]Patent: WO2006/59164,2006,A2 .Location in patent: Page/Page column 22.
[9]Patent: WO2015/148344,2015,A2 .Location in patent: Page/Page column 35; 36.
[10]Patent: JP5847362,2016,B1 .Location in patent: Paragraph 0055.
[11]Patent: TW2016/5823,2016,A .Location in patent: Paragraph 0048.
[12]Patent: US2016/289206,2016,A1 .Location in patent: Paragraph 0080; 0081.

2
[ 400777-00-6 ]
[ 351227-42-4 ]

Yield	Reaction Conditions	Operation in experiment
93%		Step c: 6-chloro-4-iodopyridin-3-amine The solution of tert-butyl 6-chloro-4-iodopyridin-3-ylcarbamate (10.0 g, 28 mmol) in 3M HCl (600 mL) was heated at 60 C. for 12 h. The mixture was allowed to cool to room temperature and treated with sat. NaHCO3 to pH=8. The aqueous layer was extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated and purified by chromatography on silica gel (10% ethyl acetate in petroleum ether as eluant) to afford 6-chloro-4-iodopyridin-3-amine (6.6 g, 93%). 1H-NMR (CDCl3, 400 MHz) delta 7.81 (s, 1H), 7.60 (s, 1H), 4.13 (br s, 2H).
90%		(6-Chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (3.67 g, 10.3 mmol) was dissolved in DCM (32 mL) and TFA (8 mL) was added. The reaction mixture was stirred at ambient temperature for 2 h and then evaporated in vacuo. The resultant residue was treated with 5N aqueous sodium hydroxide solution (25 mL), diluted with water (100 mL) and extracted into ethyl acetate (2 x 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as yellow solid (2.37 g, 90%). 1H NMR (CD3OD, 300MHz): 7.80 (s, 1H), 7.60 (s, 1H), 4.14 (s, 2H). LCMS (Method B): RT = 3.00 min, M+H+ = 255.
82%	With trifluoroacetic acid; In dichloromethane; ethyl acetate;	6-Chloro-4-iodo-3-pyridinamine Trifluoroacetic acid (2.4 mL) was added to a solution of <strong>[400777-00-6]1,1-dimethylethyl (6-chloro-4-iodo-3-pyridinyl)carbamate</strong> (Description 7, 2.2 g, 6.2 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The mixture was washed with aqueous sodium hydroxide (1M), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluding with isohexane/EtOAc (70:30), to give the title compound as a yellow solid (1.3 g, 82%). 1H NMR (360 MHz, CDCl3) delta 7.80 (1H, s), 7.60 (1H, s), and 4.13 (2H, br s). m/z (ES+) 255, 257 (M+1).

Preparation 8 : 6-Chloro-4-io The title compound was prepared according to the method described in US 2002/0022624 Al from the compound of Preparation 7. delta? (CDCl3): 4.12 (2H, br s), 7.60 (IH, s), 7.79 (IH, s).

References: [1]Patent: US2009/253736,2009,A1 .Location in patent: Page/Page column 29.
[2]Patent: WO2009/151598,2009,A1 .Location in patent: Page/Page column 122-123.
[3]Patent: US2002/22624,2002,A1 .
[4]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.
[5]Patent: WO2006/59164,2006,A2 .Location in patent: Page/Page column 22.

3
[ 5350-93-6 ]
[ 400777-00-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.
[2]Patent: US8426450,2013,B1 .
[3]Patent: WO2015/148344,2015,A2 .
[4]Patent: US9403772,2016,B2 .
[5]Inorganic Chemistry,2017,vol. 56,p. 8381 - 8389.

4
[ 24424-99-5 ]
[ 400777-00-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.
[2]Patent: US8426450,2013,B1 .
[3]Patent: WO2015/148344,2015,A2 .

5
[ 400777-00-6 ]
[ 400777-03-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.

6
[ 400777-00-6 ]
[ 400777-01-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.

7
[ 400777-00-6 ]
3-[5-chloro-2-(4-chloro-phenyl)-1-methyl-1<i>H</i>-pyrrolo[2,3-<i>c</i>]pyridin-3-yl]-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.

8
[ 400777-00-6 ]
1-{3-[5-chloro-2-(4-chlorophenyl)-1-methyl-1H-pyrrolo [2,3-c]pyridine-3-yl]-1-oxopropyl}-4-(phenylmethyl)-4-piperidinol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236.

10
[ 890122-03-9 ]
[ 400777-00-6 ]
5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [7-chloro-1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]amide [ No CAS ]
[ 890122-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 20℃; for 12h;	Preparation 64 : 5-Chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylic acid {l-[2-(tert-butyldimethyl silanyloxy)ethyl]-7-chloro-2-oxo-l,2,3,4-tetrahydroquinolin-3-yl}amide To a solution of 5-chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 16, 115mg, 0.59mmol), EDCI (132mg, 0.69mmol) and HOBt monohydrate (89mg, 0.58mmol) in DMF (1OmL) was added 3-amino-l-[2-(tert-butyldimethylsilanyloxy)ethyl]-7-chloro-3,4-dihydro-lH- quinolin-2-one (Preparation 7, 200mg, 0.56mmol) and DIPEA (220muL, 1.26mmol). The resulting solution was stirred for 12h at rt before the reaction mixture was partitioned between EtOAc (5OmL) and water/brine (10OmL, 1:1). The layers were separated and the aqueous phase was extracted with EtOAc (3x50mL), then the combined organics were washed with dilute HCl solution (IM, 5OmL), dilute NaOH solution (IM, 5OmL) and brine (5OmL). The organic phase was dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (eluent: hexane / EtOAc : 1 / 2) gave the title compound as a colourless solid. TLC (hexane / EtOAc : 1 / 3): Rf 0.60; delta? ((J6 DMSO): 0.00, 0.01 (6H, 2xs), 0.83 (9H, s), 3.14-3.21 (2H, m), 3.84-3.98 (3H, 2xm), 4.20 (IH, m), 4.78 (IH, ddd), 7.15 (IH, dd), 7.30 (IH, s), 7.34 (IH, d), 7.49 (IH, d), 7.83 (IH, s), 8.63 (IH, s), 9.15 (IH, d), 12.41 (IH, br s); m/z (ES+) = 533.19 [M+H]+; RT = 4.77 min.; Example 66: 5-Chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylic acid [7-chloro-l-(2- hydroxyethyl)-2-oxo-l,2,3,4-tetrahydroquinolin-3-yl]amide The title compound was obtained as a side product in the preparation of Preparation 64. TLC (hexane / ethyl acetate : 1 / 3): Rf 0.15; delta? (ds DMSO): 3.07-3.18 (2H, m), 3.61 (2H, m), 3.89 (IH, m), 4.04 (IH, m), 4.81 (IH, m), 4.92 (IH, appt), 7.12 (IH, dd), 7.27 (IH, s), 7.31 (IH, d), 7.43 (IH, d), 7.80 (IH, s), 8.60 (IH, s), 9.13 (IH, d), 12.36 (IH, br s); m/z (ES+) = 419.11 [M+H]+; RT = 3.42 min.

References: [1]Patent: WO2006/59164,2006,A2 .Location in patent: Page/Page column 40; 56.

11
[ 109-72-8 ]
ammonium chloride [ No CAS ]
[ 171178-45-3 ]
[ 400777-00-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With N,N,N,N,-tetramethylethylenediamine; iodine;	1,1-Dimethylethyl (6-Chloro-4-iodo-3-pyridinyl)carbamate n-Butyllithium (1.6M in hexanes, 22 mL, 35 mmol) was added dropwise to a stirred, cooled (-78 C.) solution of 1,1-dimethylethyl (6-chloro-3-pyridinyl)carbamate (Description 6, 2.68 g, 11.7 mmol) and N,N,N',N'-tetramethylethylenediamine (5.3 mL, 4.1 g, 35 mmol) in ether (60 mL). The mixture was allowed to warm to -10 C. and stirred for 2 h. The mixture was cooled to -78 C. and a cooled (-10 C.) solution of iodine (6.0 g, 24 mmol) in ether (20 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 18 h. Saturated aqueous ammonium chloride was added and the mixture was extracted with ether. The combined organic fractions were washed with aqueous sodium metabisulfite (10%), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane and the solid was collected and dried in vacuo to give the title compound as a brown solid (2.3 g, 55%). 1H NMR (400 MHz, CDCl3) delta 8.94 (1H, s), 7.73 (1H, s), 6.64 (1H, br s), and 1.54 (9H, s).

References: [1]Patent: US2002/22624,2002,A1 .

12
[ 107-00-6 ]
[ 400777-00-6 ]
[ 1072085-80-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In water; toluene; at 70℃; for 24h;Inert atmosphere; Autoclave;	Step c: tert-Butyl 4-(but-1-ynyl)-6-chloropyridin-3-ylcarbamate To a deoxygenated solution of <strong>[400777-00-6](6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester</strong> (6.0 g, 16.9 mmol), 1-butyne (9 g, 169 mmol), CuI (160.1 mg, 0.84 mmol) and triethylamine (3.4 g, 33.2 mmol) in toluene (40 mL) and water (14 mL) was added Pd(PPh3)2Cl2 (592 mg, 0.84 mmol) under N2 in a autoclave. The mixture was heated to 70 C. and stirred for 24 h. The solid was filtered off and washed with ethyl acetate (60 mL*3). The filtrate was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1) to give tert-butyl 4-(but-1-ynyl)-6-chloropyridin-3-ylcarbamate (3.5 g, 74%). 1H-NMR (CDCl3, 300 MHz) delta 9.13 (s, 1H), 7.22 (s, 1H), 6.98 (s, 1H), 2.53 (q, J=7.5 Hz, 2H), 1.54 (s, 9H), 1.29 (t, J=7.5 Hz, 3H).

References: [1]Patent: US2009/253736,2009,A1 .Location in patent: Page/Page column 26.

13
[ 917-92-0 ]
[ 400777-00-6 ]
[ 1072085-73-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In water; toluene; at 70℃; for 24h;Inert atmosphere;	Step c: [6-Chloro-4-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-carbamic acid tert-butyl ester To a deoxygenated solution of <strong>[400777-00-6](6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester</strong> (23.3 g, 65.6 mmol), 3,3-dimethyl-but-1-yne (53.8 g, 0.656 mol), CuI (623 mg, 3.3 mmol) and triethylamine (13.3 g, 0.13 mol) in toluene (150 mL) and water (50 mL) was added Pd(PPh3)2Cl2 (2.30 g, 3.28 mmol) under N2. The mixture was heated at 70 C. and stirred for 24 hours. The solid was filtered off and washed with ethyl acetate (200 mL*3). The filtrate was evaporated under reduced pressure to obtain a residue, which was purified by column (petroleum ether/ethyl acetate=10/1) to give [6-chloro-4-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (15.8 g, 78%). 1H NMR (300 MHz, CDCl3) delta 9.10 (br s, 1H), 7.21 (s, 1H), 6.98 (br s, 1H), 1.53 (s, 9H), 1.36 (s, 9H).

References: [1]Patent: US2009/253736,2009,A1 .Location in patent: Page/Page column 24-25.

14
[ 50786-62-4 ]
[ 400777-00-6 ]
[ 1072085-89-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethyl acetate; Petroleum ether; at 25℃; for 16h;	Step b: tert-Butyl 6-chloro-4-(cyclobutylethynyl)pyridin-3-ylcarbamate To the solution of tert-butyl 6-chloro-4-iodopyridin-3-ylcarbamate (7.0 g, 19.8 mmol) in Et3N (100 mL) was added the solution of ethynylcyclobutane in THF (prepared in step a), Pd(PPh3)2Cl2 (1.8 g, 2.1 mmol) and CuI (400 mg, 2.1 mmol). The reaction mixture was stirred at 25 C. for 16 h. The mixture was diluted with water and extracted with dichloromethane (3*100 mL). The extract was washed with brine, dried, concentrated in vacuo and purified by chromatography on silica gel (5-10% ethyl acetate in petroleum ether as eluant) to afford tert-butyl 6-chloro-4-(cyclobutylethynyl)pyridin-3-ylcarbamate (3.6 g, 60% yield). 1H NMR (300 MHz, CDCl3) delta: 9.11 (br, s, 1H), 7.22 (s 1H), 6.97 (s, 1H), 3.39-3.25 (m, 1H), 2.48-1.98 (m, 6H), 1.52 (s, 9H).

References: [1]Patent: US2009/253736,2009,A1 .Location in patent: Page/Page column 28.

15
[ 400777-00-6 ]
[ 74-88-4 ]
[ 825643-58-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		To a solution of 1.00 g (2.82 mmol) <strong>[400777-00-6](6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester</strong> in 10 ml DMF were added 0.12 g (3.1 mmol) sodium hydride (60% in mineral oil) at -10 C. (The preparation of <strong>[400777-00-6](6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester</strong> has been described in US 2002/0022624 A1.) The reaction mixture was allowed to warm to room temperature. After 1 h, the mixture was cooled back to -10 C., and 0.44 ml (7.1 mmol) iodomethane were added during 5 min. The reaction mixture was allowed to warm to room temperature. After 2.5 at room temperature, the reaction was quenched by addition of 10 ml of a saturated aqueous solution of NaHCO3 and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, hexanes/ethyl acetate=4:1) to give 1.06 g (100%) of the title compound as a colorless oil. MS m/e (%): 368 (M+, 1)
63 g		Step 3 To the solution of <strong>[400777-00-6]tert-butyl (6-chloro-4-iodopyridin-3-yl)carbamate</strong> (61 g, 0.172 mol) in 300 mL of anhydrous THF was added 60% NaH (7.6 g, 0.189 mol) at 0 C. under N2 atmosphere. After the addition was finished, the solution was stirred for 30 min, and then the solution of MeI (26.92 g, 0.189 mol) in 100 mL of dry THF was added. Then the solution was stirred at 0 C. for 3 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to afford 63 g of crude tert-butyl (6-chloro-4-iodopyridin-3-yl)(methyl)carbamate used into the following de-protection without the further purification.
		Step 3: (0191) To the solution of tert-butyl(6-chloro-4-iodopyridin-3-yl)carbamate (61 g, 0.172 mol) in 300 mL of anhydrous THF was added 60% NaH (7.6 g, 0.189 mol) at 0 C. under N2 atmosphere. After the addition was finished, the solution was stirred for 30 min, and then the solution of MeI (26.92 g, 0.189 mol) in 100 mL of dry THF was added. Then the solution was stirred at 0 C. for 3 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to afford 63 g of crude tert-butyl(6-chloro-4-iodopyridin-3-yl)(methyl)carbamate used into the following de-protection without the further purification

2.66 g	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 0.5h;Cooling with ice;	To N,N-dimethylformamide (30 mL) solution of (6-chloro-4-iodo-pyridin-3-yl)carbamic acid tert- butyl (2.59 g), under ice-cooling, sodium hydride (content60%, 0 .32g) was added, and the mixture was stirred for 30 minutes at roomtemperature. Under ice-cooling, methyl iodide (2.60g) was added to the mixture, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium bicarbonate solution was added to the reactionmixture, followed by extraction with ethyl acetate. The organic layer waswashed with water, saturated brine, & dried over anhydrous magnesiumsulfate, and then distilled off under reduced pressure. The crude productobtained was purified by aminopropyl silyl silica gel column chromatography(eluting solvent: n- hexane / ethyl acetate = 100/0 to 70/30) to give the titlecompound (2.66 g).
2.66 g		Reference Example 5 (0082) (6-Chloro-4-iodopyridin-3-yl)methylcarbamic acid tert-butyl ester (0083) To a solution of (6-Chloro-4-iodopyridin-3-yl)carbamic acid tert-butyl ester (2.59 g) in N,N-dimethylformamide (30 mL) was added sodium hydride (60%, 0.32 g) under ice-cooling, and the mixture was stifled at room temperature for 30 minutes. To the mixture was added iodomethane (2.60 g) under ice-cooling and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. (0084) The obtained crude product was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (2.66 g).
		To the solution of <strong>[400777-00-6]tert-butyl (6-chloro-4-iodopyridin-3-yl)carbamate</strong> (61 g, 0.172 mol) in 300 mL of anhydrous THF was added 60% NaH (7.6 g, 0.189 mol) at 0 C. under N2atmosphere. After the addition was finished, the solution was stirred for 30 min, and then the solution of MeI (26.92 g, 0.189 mol) in 100 mL of dry THF was added. Then the solution was stirred at 0 C. for 3 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to afford 63 g of crude tert-butyl (6-chloro-4-iodopyridin-3-yl)(methyl)carbamate used into the following de-protection without the further purification.

References: [1]Patent: US2006/30600,2006,A1 .Location in patent: Page/Page column 13.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3405 - 3408.
[3]Patent: US8426450,2013,B1 .Location in patent: Page/Page column 28; 29.
[4]Patent: US9403772,2016,B2 .Location in patent: Page/Page column 33.
[5]Patent: JP5847362,2016,B1 .Location in patent: Paragraph 0056.
[6]Patent: US2016/289206,2016,A1 .Location in patent: Paragraph 0082; 0083; 0084.
[7]Patent: JP2015/17121,2015,A .Location in patent: Paragraph 0164; 0167.

16
[ 400777-00-6 ]
[ 825643-59-2 ]

References: [1]Patent: US8426450,2013,B1 .
[2]Patent: US9403772,2016,B2 .
[3]Patent: JP5847362,2016,B1 .
[4]Patent: US2016/289206,2016,A1 .
[5]Patent: JP2015/17121,2015,A .

17
[ 400777-00-6 ]
(6-chloro-4-ortho-tolylpyridine-3-yl) methylamine [ No CAS ]

References: [1]Patent: US9403772,2016,B2 .
[2]Patent: JP5847362,2016,B1 .
[3]Patent: US2016/289206,2016,A1 .
[4]Patent: JP2015/17121,2015,A .
[5]Patent: US8426450,2013,B1 .

18
[ 400777-00-6 ]
[ 401891-55-2 ]

References: [1]Patent: US9403772,2016,B2 .
[2]Patent: US2016/289206,2016,A1 .
[3]Patent: JP2015/17121,2015,A .
[4]Patent: US8426450,2013,B1 .

19
[ 400777-00-6 ]
[ 1431216-67-9 ]

References: [1]Patent: US9403772,2016,B2 .
[2]Patent: JP2015/17121,2015,A .
[3]Patent: US8426450,2013,B1 .

20
[ 400777-00-6 ]
[ 1431216-62-4 ]

References: [1]Patent: US9403772,2016,B2 .
[2]Patent: JP2015/17121,2015,A .
[3]Patent: US8426450,2013,B1 .

21
[ 400777-00-6 ]
[ 1431216-60-2 ]

References: [1]Patent: US9403772,2016,B2 .
[2]Patent: JP2015/17121,2015,A .
[3]Patent: US8426450,2013,B1 .

22
[ 400777-00-6 ]
[ 98-80-6 ]
tert-butyl (6-chloro-4-phenylpyridin-3-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; sodium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 90℃; for 18h;Inert atmosphere;	Step C: tert-Butyl (6-chloro-4-phenylpyridin-3-yl)carbamateA deoxygenated mixture of ?-butyl (6-chloro-4-iodopyridin-3-yl)carbamate (5.30 g, 14.9 mmol), phenylboronic acid (2.00 g, 16.4 mmol), Pd(OAc)2 (0.168 g, 0.747 mmol), Ph3P (0.392 g, 1.49 mmol), and aqueous a2C03 solution (2 M, 37.4 mL, 74.7 mmol) in DME (150 mL) was heated at 90 C under 2 atmosphere for 18 h. The mixture was cooled, silica gel (15 g) was added, and the resulting mixture was concentrated. The residue was purified by column chromatography on silica gel (PE:EtOAc : EtsN = 95 : 5 : 1) to give the title compound. MS: m/z = 305 (M + 1). XH NMR (400 MHz, CDC13) delta 9.08 (s, 1H), 7.48-7.55 (m, 3H), 7.34-7.36 (m, 2H), 7.16 (s, 1H), 6.35 (s, 1H), 1.45 (s, 9H).

References: [1]Patent: WO2015/148344,2015,A2 .Location in patent: Page/Page column 36; 37.

23
[ 400777-00-6 ]
[ 1431216-61-3 ]

References: [1]Patent: US9403772,2016,B2 .

24
[ 400777-00-6 ]
2-[5'-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4'-(4-fluoro-2-methylphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-2-methylpropionic acid ethyl ester [ No CAS ]

References: [1]Patent: US2016/289206,2016,A1 .

25
[ 400777-00-6 ]
2-[5'-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropanoyl]methylamino}-4'-(4-fluoro-2-methylphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]propionic acid ethyl ester [ No CAS ]

References: [1]Patent: US2016/289206,2016,A1 .

26
[ 400777-00-6 ]
[5'-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4'-(4-fluoro-2-methylphenyl)-3-methoxyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]acetic acid [ No CAS ]

References: [1]Patent: US2016/289206,2016,A1 .

27
[ 400777-00-6 ]
2-[5'-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropanoyl]methylamino}-4'-(4-fluoro-2-methylphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-2-methylpropanoic acid [ No CAS ]

References: [1]Patent: US2016/289206,2016,A1 .

28
[ 400777-00-6 ]
[6-chloro-4-(4-fluoro-2-methylphenyl)pyridin-3-yl] methylamine [ No CAS ]

References: [1]Patent: JP5847362,2016,B1 .
[2]Patent: US2016/289206,2016,A1 .

29
[ 400777-00-6 ]
[ 825643-73-0 ]

References: [1]Patent: JP5847362,2016,B1 .
[2]Patent: US2016/289206,2016,A1 .

30
[ 400777-00-6 ]
[5'-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4'-(4-fluoro-2-methylphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]acetic acid ethyl ester [ No CAS ]

References: [1]Patent: US2016/289206,2016,A1 .

31
[ 400777-00-6 ]
[5'-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4'-(4-fluoro-2-methyl phenyl)-3-methoxyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]acetic acid ethyl ester [ No CAS ]

References: [1]Patent: US2016/289206,2016,A1 .

32
[ 400777-00-6 ]
ethyl 4-[5-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4-(4-fluoro-2-methylphenyl)pyridin-2-yl]cyclohex-3-ene carboxylic acid [ No CAS ]

References: [1]Patent: JP5847362,2016,B1 .

33
[ 400777-00-6 ]
2-(3,5-bistrifluoromethylphenyl)-N-[6-(1,4-dioxaspiro[4,5]dec-7-ene-8-yl)-4-(4-fluoro-2-methylphenyl) pyridin-3-yl]-N-methylisobutyramide [ No CAS ]

References: [1]Patent: JP5847362,2016,B1 .

34
[ 400777-00-6 ]
ethyl 2-{4-[5-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4-(4-fluoro-2-methylphenyl)pyridin-2-yl]cyclohex-3-enyl}-2-methylpropionic acid [ No CAS ]

References: [1]Patent: JP5847362,2016,B1 .

35
[ 400777-00-6 ]
{4-[5-[2-(3,5-bistrifluoromethylphenyl)-2-methylpropionyl]methylamino}-4-(4-fluoro-2-methylphenyl)pyridin-2-yl]cyclohex-3-enyl}methyl acetate [ No CAS ]

References: [1]Patent: JP5847362,2016,B1 .
[2]Patent: JP5847362,2016,B1 .

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

Related Functional Groups of
[ 400777-00-6 ]

Chlorides

A228692 [171178-45-3]

tert-Butyl (6-chloropyridin-3-yl)carbamate

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tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate

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tert-Butyl ((6-chloropyridin-2-yl)methyl)carbamate

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A154234 [501907-61-5]

tert-Butyl (2,6-dichloropyridin-4-yl)carbamate

Similarity: 0.68

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tert-Butyl (6-chloro-3-iodopyridin-2-yl)carbamate

Similarity: 0.68

Amides

A174361 [154048-89-2]

N-Boc-3-Amino-4-iodopyridine

Similarity: 0.86

A228692 [171178-45-3]

tert-Butyl (6-chloropyridin-3-yl)carbamate

Similarity: 0.82

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N-Boc-4-Amino-3-iodopyridine

Similarity: 0.76

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tert-Butyl (4-iodo-2-methoxypyridin-3-yl)carbamate

Similarity: 0.74

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tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate

Similarity: 0.72

Amines

A174361 [154048-89-2]

N-Boc-3-Amino-4-iodopyridine

Similarity: 0.86

A228692 [171178-45-3]

tert-Butyl (6-chloropyridin-3-yl)carbamate

Similarity: 0.82

A130495 [211029-67-3]

N-Boc-4-Amino-3-iodopyridine

Similarity: 0.76

A191509 [162709-20-8]

tert-Butyl (4-iodo-2-methoxypyridin-3-yl)carbamate

Similarity: 0.74

A182898 [1227958-32-8]

tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate

Similarity: 0.72

Related Parent Nucleus of
[ 400777-00-6 ]

Pyridines

A174361 [154048-89-2]

N-Boc-3-Amino-4-iodopyridine

Similarity: 0.86

A228692 [171178-45-3]

tert-Butyl (6-chloropyridin-3-yl)carbamate

Similarity: 0.82

A130495 [211029-67-3]

N-Boc-4-Amino-3-iodopyridine

Similarity: 0.76

A191509 [162709-20-8]

tert-Butyl (4-iodo-2-methoxypyridin-3-yl)carbamate

Similarity: 0.74

A182898 [1227958-32-8]

tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate

Similarity: 0.72

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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

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CAS No.: 400777-00-6

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CAS No.: 400777-00-6

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[ 400777-00-6 ] Synthesis Path-Downstream 1~35

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[ 400777-00-6 ]

Chlorides

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Pyridines

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{[proInfo.proName]}

CAS No.: 400777-00-6

{[proInfo.proName]}

CAS No.: 400777-00-6

Alternative Products

Product Details of [ 400777-00-6 ]

Safety of [ 400777-00-6 ]

Computational Chemistry of [ 400777-00-6 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 400777-00-6 ]

[ 400777-00-6 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 400777-00-6 ]

Chlorides

Amides

Amines

Related Parent Nucleus of [ 400777-00-6 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 400777-00-6 ]

Related Parent Nucleus of
[ 400777-00-6 ]