[ CAS No. 7544-75-4 ] {[proInfo.proName]}

Name: 7544-75-4|3,4-Dihydro-2H-pyrrol-5-amine hydrochloride|95%
Brand: Ambeed
SKU: A121758
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Quality Control of [ 7544-75-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7544-75-4 ]

SDS Specification

Alternatived Products of [ 7544-75-4 ]

Product Details of [ 7544-75-4 ]

CAS No. :	7544-75-4	MDL No. :	MFCD00790772
Formula :	C₄H₉ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JEBHLIYFPKISBI-UHFFFAOYSA-N
M.W :	120.58	Pubchem ID :	12778905
Synonyms :

Calculated chemistry of [ 7544-75-4 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.91
TPSA :	38.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.09
Log Po/w (WLOGP) :	0.56
Log Po/w (MLOGP) :	0.5
Log Po/w (SILICOS-IT) :	1.35
Consensus Log Po/w :	0.46

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.53
Solubility :	35.5 mg/ml ; 0.295 mol/l
Class :	Very soluble
Log S (Ali) :	-0.26
Solubility :	65.7 mg/ml ; 0.545 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.55
Solubility :	33.8 mg/ml ; 0.28 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.72

Safety of [ 7544-75-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7544-75-4 ]

* 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 [ 7544-75-4 ]
Downstream synthetic route of [ 7544-75-4 ]

[ 7544-75-4 ] Synthesis Path-Upstream 1~2

1
[ 628-20-6 ]
[ 7544-75-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With ammonia In ethanol at -78 - 120℃; for 16.75 h; Autoclave	Precursor 4: 3-Bromo-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 1) Pyrrolidin-2-imine hydrochloride In a 250 mL bottomed flask, ammonia was bubbled into ethanol (80 mL) that was cooled to -78° C. for 45 min. The thus obtained saturated solution was transferred to a Parr autoclave, which contained 4-chlorobutanenitrile (60 g, 580 mmol) and the mixture was stirred and heated to 120° C. for 16 hr. The reaction mixture was cooled and transferred to a round-bottomed flask and the solvent was removed under reduced pressure to afford a yellow solid, which was washed with diethyl ether and dried under high vacuum to afford an off-white solid, 19.5 g, 232 mmol, 40percent yield. ¹H NMR (DMSO-d6) δ 9.22 (br s, 1H), 8.93 (br s, 1H), 7.60 (br s, 1H), 3.52 (d, J=7.2 Hz, 2H), 2.76 (d. J=8.0 Hz, 2H), 2.08-1.96 (m, 2H).

Reference： [1] Patent: US2014/148461, 2014, A1, . Location in patent: Paragraph 0354-0355

2
[ 66996-69-8 ]
[ 7544-75-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 5, p. 999 - 1001

[ 7544-75-4 ] Synthesis Path-Downstream 1~33

1
[ 898-22-6 ]
[ 7544-75-4 ]
2,4-Bis(ethoxycarbonyl)-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 4950 - 4955

Yield	Reaction Conditions	Operation in experiment
		1-Aza-2-imino-cyclopentane hydrochloride: 1 H NMR(CDCl3): 9.44, 9.13 & 8.77 (3br, N--H's), 2.88 (t, CH2 N), 2.88 (t, CH2 C=N), 2.10(m). Mass Spectrum m/e=84.9 (M+1).

4
[ 7544-75-4 ]
[ 792909-14-9 ]
5-Chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-3H-pyrimidin-4-one hydrochlorid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5247 - 5250

5
[ 430440-92-9 ]
[ 7544-75-4 ]
6-(2-imino-pyrrolidin-1-ylmethyl)-5-methyl-1<i>H</i>-pyrimidine-2,4-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3443 - 3450

6
[ 73742-45-7 ]
[ 7544-75-4 ]
Tipiracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 20℃; for 3.0h;Reflux;	At room temperature, anhydrous methanol (500 ml),<strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong> (45g), DBU (100g) was added to the reaction flask,After stirring until all was dissolved, Compound 4 (50 g) was added to the above reaction solution.After the addition, the temperature is raised at reflux temperature for at least 3 hours.The hot filter and the filter cake were rinsed with a small amount of methanol, suction filtered, and the filter cake was beaten with purified water, suction filtered, and the filter cake was rinsed with a small amount of ethanol, and blast dried to obtain a white solid 42 g.That is, 5-chloro-6-[(2-imino-1-pyrrolidine)methyl]-2,4(1H,3H)-pyrimidinedione,The yield was 84%.
80 g	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 25 - 65℃;	To a stirred solution of <strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong> (79.9 g; 0.66 mol) in methanol (1000 ml), DBU (194.9 g; 1.28 mol) was added at 25-30C. Thereafter, 5-Chloro-6-chloromethyluracil (100 g; 0.51 mol) was added and stirred the suspension at 60-65C for 4-5 h. The reaction mixture was cooled to 25-30C and stirred for another 2-3h. The solid product was filtered, washed with methanol (300 ml) and dried under reduced pressure (10-20 mmHg) at 45-50C to obtain Tipiracil crude. (0042) Yield: 98.2 g (0043) Chromatographic purity by HPLC: > 98%; Tipiracil crude (90 g; 0.37 mol) was suspended in DM water (900 ml) at 25- 30C. The pH of above suspension was adjusted to 4.0-4.2 using glacial acetic acid (50 ml) at 25-30C to obtain clear solution. Further the solution was neutralized with 10% sodium hydroxide solution (pH: 6.5-7.0) at 25- 30C, during which product precipitates out. Thereafter the slurry was stirred for another 2h at 25-30C. Finally, the product was filtered, washed with DM water (180 ml) and dried under reduced pressure (10-20 mmHg) at 50-55 C to obtain pure Tipiracil. (0046) Yield: 80 g (0047) Chromatographic purity by HPLC: > 99.7% (0048) Polymorph - XRPD represented as Figure 3
95 g	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 0 - 70℃; for 8.0h;	1 ,8-Diazabicyclo[5.4.0]undec-7-ene (203 gm) was slowly added to a pre-cooled mixture of S -chloro-6-(chloromethyl)pyrimidine-2,4( 1 H,3H)-dione compound of formula-3a (100 gm), <strong>[7544-75-4]pyrrolidin-2-imine hydrochloride</strong> salt compound of formula-4a (74.2 gm) and methanol (1000 ml) at 0-5C. Heated the reaction mixture to 65-70C and stined for 8 hrs at the same temperature. Cooled the reaction mixture to 0-5C and stined for 2 hrs at the same temperature. Filtered the solid, washed with methanol and suck dried the material to get the title compound.The PXRD pattern of the obtained compound is shown in figure-9.Yield: 9S gm; Purity by HPLC: 97.6S%.

Reference： [1]Patent: CN104945384,2018,B .Location in patent: Paragraph 0053; 0054; 0055; 0056
[2]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3443 - 3450
[3]Patent: WO2019/53574,2019,A1 .Location in patent: Page/Page column 10-11
[4]Patent: WO2019/49174,2019,A1 .Location in patent: Page/Page column 32

7
[ 7544-75-4 ]
[ 183205-46-1 ]
TPI(Br) [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3443 - 3450

8
[ 66996-69-8 ]
[ 7544-75-4 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 999 - 1001

9
[ 17694-68-7 ]
[ 7544-75-4 ]
[ 408498-43-1 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 999 - 1001

10
[ 17570-98-8 ]
[ 7544-75-4 ]
[ 408498-42-0 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 999 - 1001

11
[ 7544-75-4 ]
[ 70-11-1 ]
[ 107392-72-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium carbonate; In DMF (N,N-dimethyl-formamide); at 80℃; for 18.0h;	2-Phenyl-6,7-dihydro-5H-pyrrolo[1, 2-a] imidazole; Combine <strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong> (6. 98 g, 57. 8 mmol) (Callahan, et al., (at) J. Med. Chem. 45, 999-1001 (2002)), 2-bromoacetophenone (3. 8 g, 19. 3 mmol), and sodium carbonate (8. 2 g, 77. 2 mmol) in dry dimethylformamide (25 mL). Heat at 80C for 18 hours. Cool to room temperature, add water (60 mL), and extract with ethyl acetate (3 x 100 mL). Concentrate the combined organic layers under reduced pressure. Dilute the residue with diethyl ether (100 mL), wash with cold water (3 x 80 mL), and concentrate under reduced pressure to provide the desired compound as a white solid (3. 2 g, 89 %). MS (ES) : m/z = 185. 1 (M++H)
89%	With sodium carbonate; In DMF (N,N-dimethyl-formamide); at 80℃; for 18.0h;	Prepare <strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong> (6. 98 g, 57.8 mmol) according to Callahan, et al., J. Med. Chem. 2002,45, 999-1001) and combine 2-bromoacetophenone (3.8 g, 19.3 mmol) with Na2CO3 (8.2 g, 77.2 mmol) in dry DMF (25 [ML)] and heat at [80C] for 18 hours. Then, cool the mixture to room temperature, add water (60 mL), and extract with EtOAc (3 x 100 mL). Concentrate the combined organic layers in vacuo, dilute the residue with ether (100 mL), and wash with cooled water (3 x 80 mL). Concentrate the organic layer in vacuo to give a white solid, 3.2 g, 89 [%] yield. MS [(ES+)] : [IIZLZ] = 185. 1 [(M+H) +]
39%	With sodium carbonate; In ISOPROPYLAMIDE; at 80℃; for 15.0h;	(1) A DMA (35 ml) suspension containing Compound 1 (5.57 g, 28 mmol), Compound 2 (10 g, 83 mmol) and sodium carbonate (12 g, 113 mmol) was stirred at 80 C. for 15 hours under argon atmosphere. After cooling by allowing to stand, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:2) to give Compound 3 (2.02 g, 11 mmol, 39%) as a solid.

Reference： [1]Patent: WO2005/80380,2005,A1 .Location in patent: Page/Page column 30
[2]Patent: WO2004/14900,2004,A1 .Location in patent: Page 44
[3]Patent: US2008/9506,2008,A1 .Location in patent: Page/Page column 31

12
[ 623564-39-6 ]
[ 7544-75-4 ]
[ 623564-38-5 ]

Yield	Reaction Conditions	Operation in experiment
41%		Example 13; Preparation of (5R). (6Z)-6- (6, 7-Dihvdro-SH-pyrrolorl. 2-alimideizol-2-vlmethylene) 7-oxo-4-thia-1-aza-bicvclor3. 2. Olhept-2-ene-2-carboxylic acid, sodium salt Step 1: 6, 7-Dihydro-5H-pyrrolo [1, 2-a] imidazole-2-carbaldehyde 28% Sodium methoxide (5.26g) was added to the EtOH (250 mL) solution of 4,5- dihydro-3H-pyrrol-2-ylamine hydrochloride (3.27g) at room temperature. After stirring for 5 min at room temperature, 2-bromo-3-propoxy-propenal (5.79g) was added to the mixture at room temperature, then the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was taken to dryness in vacuo. The residue was dissolved in CHCI3 (300 mL) and triethylamine (3.8 mL) was added. The mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, washed with 50% K2CO3, dried over anhydrous K2CO3, filtered, and evaporated under reduced pressure. The residue was applied with silicagel column chromatography, eluted with CHCI3-acetone (2: 1), and 6, 7-Dihydro-5H-pyrrolo [1,2-a] imidazole-2- carbaldehyde (41%, 1. 51g) was obtained as a pale yellow solid. 'H NMR (d, CDCI3) : 2.62-2. 7 (m, 2H), 2.90-2. 94 (m, 2H), 4.07 (t, 2H, J = 7.2 Hz), 7.59 (s, 1H), 9.80 (s, 1H).

Reference： [1]Patent: WO2003/93277,2003,A1 .Location in patent: Page/Page column 80-81

13
[ 7544-75-4 ]
[ 5843-43-6 ]
[ 133365-44-3 ]

Yield	Reaction Conditions	Operation in experiment
		1) 7,8-Dihydro-2H,6H-pyrrolo[1,2-a]-1,3,5-triazine-2,4(3H)-dione In the manner described in Example 1--1), the entitled compound was obtained as colorless crystals from <strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong> and phenoxycarbonylisocyanate. Melting Point: 201-202 C. NMR Spectrum (DMSO-d6): 2.87 (2H, t), 2.07 (2H, t), 3.82 (2H, t), 11.25 (1H, bs) IR Spectrum nu (KBr) cm-1: 3430, 3210, 3080, 1740, 1710, 1690, 1630, 1440, 1410

Reference： [1]Patent: US5232924,1993,A

14
[ 5349-17-7 ]
[ 7544-75-4 ]
[ 122454-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N-methyl-acetamide; methylene chloride acetone; water;	EXAMPLE 19 2-(4-Pyridyl) 6,7 dihydro [5H]-pyrrolo[1,2 a]imidazole A stirred suspension of 10q (35.6 mmoles) of 4-(bromoacetyl) pyridine hydrobromide and 12.9 q (107 mmoles) of 2-imino-pyrrolidine hydrochloride in 100 ml of dry dimethylformamide was treated with 18.9 q (178 mmoles) of anhydrous sodium carbonate. This suspension was heated at 80 C. overnight in an oil bath. The solvent was removed in vacuo, the residue dissolved in water and extracted with chloroform. The organic layer was washed three times with water, dried over anhydrous potassium carbonate and stripped in vacuo. The residue was chromatographed on silica and eluted with 10-15% methanol in methylene chloride acetone (85:15). This fraction was stripped in vacuo and the solid residue recrystallized twice from ethyl acetate to afford the desired titled compound, mp 140-141 C., 1 H-NMR (250 MHz, CDCl3) delta8 62 (2H,d), 7.60(2H,d), 7.34(lH,s), 4.04(2H,t), 2.95 (2H,t), 2.64(2H,q).

Reference： [1]Patent: US5002941,1991,A

15
[ 324558-30-7 ]
[ 7544-75-4 ]
[ 6674-22-2 ]
4-Oxo-2-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	EXAMPLE 126 4-Oxo-2-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-3-carbonitrile In analogy to the procedure described in example 17 the Z and/or E 2-cyano-3-methylsulfanyl-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acrylic acid ethyl ester [example 13 a)] was treated with <strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong> [J. Med. Chem. (1996), 39, 669-672] and 1,8-diazabicyclo[5.4.0]undec-7-en in N,N-dimethylformamide at 100 C. to yield the 4-oxo-2-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-4,6,7,8-tetrahydro-pyrrolo [1,2-a]pyrimidine-3-carbonitrile as colorless solid; m.p. 184.5-190.5 C.; MS: [M+H]+=307.

Reference： [1]Patent: US6218385,2001,B1

16
2-bromo-3-propoxy-propenal [ No CAS ]
[ 7544-75-4 ]
[ 623564-38-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; triethylamine; In ethanol; chloroform;	Step 1 6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-2-carbaldehyde 28% Sodium methoxide (5.26 g) was added to the EtOH (250 mL) solution of 4,5-dihydro-3H-pyrrol-2-ylamine hydrochloride (3.27 g) at room temperature. After stirring for 5 min at room temperature, 2-bromo-3-propoxy-propenal (5.79 g) was added to the mixture at room temperature, then the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was taken to dryness in vacuo. The residue was dissolved in CHCl3 (300 mL) and triethylamine (3.8 mL) was added. The mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, washed with 50% K2CO3, dried over anhydrous K2CO3, filtered, and evaporated under reduced pressure. The residue was applied with silicagel column chromatography, eluted with CHCl3-acetone (2:1), and 6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-2-carbaldehyde (41%, 1.51 g) was obtained as a pale yellow solid. 1H NMR (d, CDCl3): 2.62-2.7 (m, 2H), 2.90-2.94 (m, 2H), 4.07 (t, 2H, J=7.2 Hz), 7.59 (s, 1H), 9.80 (s, 1H).

Reference： [1]Patent: US2004/132708,2004,A1

17
[ 73742-45-7 ]
[ 7544-75-4 ]
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
475.5 g	With sodium ethanolate; In N,N-dimethyl-formamide; at 20℃; for 10.0h;	In a 20 L reaction flask, 5-chloro-6-chloromethyluracil (950.0 g, 4.87 mol) was added to 9500 mL of DMF, mechanical stirring was started and 2-aminopyrrolidine hydrochloride 1175.0g, 9.74mol). The temperature of the system was maintained at 20 C in a water bath. Sodium ethoxide (994.6g, 14.61mol) was added in portions and stirred for 10h with a large amount of white solid. TLC was followed by disappearance of the 5-chloro-6-chloromethyluracil point reaction (methylene chloride: methanol = 10: 1) and the reaction was completed. Ice bath, the control temperature below 30 , 9500mL water was added to the reaction mixture, stirred for 30min, suction filtered. The resulting solid was air-dried at 60 C for 6 hours to give 685.6 g of crude white substitute pipirin as a white solid.In a 20 L reaction flask, the crude pimazine (680.0 g, 2.80 mol) was added to 6800 mL of ethanol, mechanically stirred, 3400 mL of water and 2000 mL of 1M HCl were added and the mixture was heated to reflux (75 C) The filtrate was filtered and the filtrate was stirred at room temperature (20 C) for 10 hours with stirring. The mixture was filtered with suction, and the resulting solid was air-dried for 12 hours at 60 C to obtain 475.5 g of white solid hydrochloride.

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1248 - 1260
[2]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 49 - 54
[3]Patent: CN106892902,2017,A .Location in patent: Paragraph 0103; 0106; 0107; 0108

18
[ 7544-75-4 ]
[ 792909-14-9 ]
5-chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-3H-pyrimidin-4-one hydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1248 - 1260

19
[ 7544-75-4 ]
[ 700-55-0 ]
[ 1243510-75-9 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 49 - 54

20
[ 7544-75-4 ]
[ 183205-46-1 ]
5-bromo-6-[(2-iminopyrrolidin-1-yl)methyl]uracil hydrochloride [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2009,vol. 52,p. 146 - 150
[2]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 49 - 54

21
[ 7544-75-4 ]
[ 183205-42-7 ]
6-[(2-iminopyrrolidinyl)methyl]-5-iodouracil hydrochloride [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2009,vol. 52,p. 146 - 150

22
[ 344-00-3 ]
[ 7544-75-4 ]
[ 1221577-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In methanol for 24h; Reflux;	1.B Step B: Preparation of 7,8-dihydro-3-methyl-2-(trifluoromethyl)pyrrolo[1,2-α]pyrimidin-4(6H)-one To a stirred solution of 3,4-dihydro-2H-pyrrol-5-amine hydrochloride (1:1) (i.e. the product of Step A) (2.00 g, 16.6 mmol) in methanol (30 mL) was added ethyl 4,4,4-trifluoro-2-methyl-3-oxobutanoate (3.30 g, 16.6 mmol), followed by a solution of sodium methoxide (30 wt %, 8.50 g, 50.0 mmol). The reaction mixture was warmed to reflux and stirred for 24 h. Then the reaction mixture was concentrated under reduced pressure. To the residue was added water (50 mL), followed by 1 N hydrochloric acid until the pH was 2-3, and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the title product as a white solid (2.3 g), which was used without further purification in the next step. 1H NMR (CDCl3) δ 4.18 (m, 2H), 3.16 (m, 2H), 2.23-2.29 (m, 5H).

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US2010/99561, 2010, A1 Location in patent: Page/Page column 19

23
[ 628-20-6 ]
[ 7544-75-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With ammonia; In ethanol; at -78 - 120℃; for 16.75h;Autoclave;	Precursor 4: 3-Bromo-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 1) Pyrrolidin-2-imine hydrochloride In a 250 mL bottomed flask, ammonia was bubbled into ethanol (80 mL) that was cooled to -78 C. for 45 min. The thus obtained saturated solution was transferred to a Parr autoclave, which contained 4-chlorobutanenitrile (60 g, 580 mmol) and the mixture was stirred and heated to 120 C. for 16 hr. The reaction mixture was cooled and transferred to a round-bottomed flask and the solvent was removed under reduced pressure to afford a yellow solid, which was washed with diethyl ether and dried under high vacuum to afford an off-white solid, 19.5 g, 232 mmol, 40% yield. 1H NMR (DMSO-d6) delta 9.22 (br s, 1H), 8.93 (br s, 1H), 7.60 (br s, 1H), 3.52 (d, J=7.2 Hz, 2H), 2.76 (d. J=8.0 Hz, 2H), 2.08-1.96 (m, 2H).

Reference： [1]Patent: US2014/148461,2014,A1 .Location in patent: Paragraph 0354-0355

24
[ 6221-13-2 ]
[ 7544-75-4 ]
[ 122454-71-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16.0h;	2) 2-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole A mixture of 2-bromo-1-(pyridin-4-yl)ethanone (12.8 g, 64 mmol), <strong>[7544-75-4]pyrrolidin-2-imine hydrochloride</strong> (10.8 g, 89.4 mmol) and Na2CO3 (33.8 g, 319 mmol) in DMF (65 mL) was stirred and heated to 80 C. in a 250 mL three-necked flask for 16 hrs. The mixture was cooled to 22 C. and poured into water (500 mL). The product was partitioned between ethyl acetate (300 mL) and aqueous phase. The aqueous phase was extracted three time with ethyl acetate (300 mL each). The combined organic phases were washed with water, then brine and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated to afford grey solid, 2-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (7.03 g, 38 mmol), 60% yield.

Reference： [1]Patent: US2014/148461,2014,A1 .Location in patent: Paragraph 0356

25
[ 17570-98-8 ]
[ 7544-75-4 ]
[ 408498-42-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium carbonate; In N,N-dimethyl-formamide; at 80℃; for 18h;	Step 1 : A mixture of 2-bromo- 1 -(pyridin-2-yl)ethan- 1 -one hydrobromide (1.4 g, 5.0 mmol), 3,4-dihydro-2H-pyrrol-5-amine hydrochloride (2.5 g, 20 mmol) and Na2C03 (3.2 g, 30 mmol) in DMF (20 mL) was stirred at 80 C for 18 h. After cooling to room temperature, the reaction mixture was then partitioned between water and dichloromethane. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue, which was purified by chromatography eluting with dichloromethane/methanol/ammonium hydroxide (15/1/0.05) to provide 2-(pyridin-2-yl)-6,7- dihydro-5H-pyrrolo[l,2-a]imidazole as a brown oil (0.8 g, 86%).

Reference： [1]Patent: WO2016/81364,2016,A1 .Location in patent: Paragraph 0504

26
[ 18592-13-7 ]
[ 7544-75-4 ]
6-(1-(2-iminopyrrolidin-1-yl)methyl)uracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.23%	With triethylamine; In acetonitrile; at 70℃;	In 500mL three-necked flask,Add 250 mL of acetonitrile,16 grams of Compound I (100 mmol),12 grams of Compound II (100 mmol),Stirring,Heated to 70 C,Add dropwise 10 mL of triethylamine,Reaction for at least 4h.TLC monitoring the progress of the reaction,The reaction is completed.Cool to room temperature,The solvent was distilled off under reduced pressure,Add 100mL water,Ethyl acetate twice,Each 50mL.The organic phase is washed twice with saturated sodium chloride solution,Dried over anhydrous sodium sulfate 2h,Filter out the desiccant,Evaporate the ethyl acetate,19.6 g of a white solid was obtained in a yield of 94.23%.

Reference： [1]Patent: CN106317028,2017,A .Location in patent: Paragraph 0041; 0042; 0043; 0044; 0045; 0051; 0052; 0053

27
5-chloro-6-(hydroxymethyl)-2 4-(1H,3H)-pyrimidinedione [ No CAS ]
[ 7544-75-4 ]
Tipiracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol;Reflux;	The 18.6g <strong>[7544-75-4]2-iminopyrrolidine hydrochloride</strong>, 250ml of methanol were added to the reaction flask followed by stirring to clear, dropwise 46.7g DBU, completed.Add 20g 5-chloro-6-hydroxymethyluracil, the reaction was heated to reflux for 2-4 hours, TLC monitoring reaction; cooled to room temperature, filtered, the filter cake was washed with 100ml of methanol, and dried to give a white solid.

Reference： [1]Patent: CN107298656,2017,A .Location in patent: Paragraph 0086; 0089

28
[ 73742-45-7 ]
[ 7544-75-4 ]
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.6%		Adding to the reaction bottle 150 ml N, N - dimethyl formamide (DMF), 19.5g 2 - amino pyrrolidine hydrochloride, 18.0g sodium ethoxide, 15.0g 5 - chloro -6 - chloro methyl uracil, 30 C stirring reaction 6 - 7h, will suspend the reaction filter, cake 15 - 20ml ethanol washing the filter cake; in 75 - 80 C under the conditions, the obtained filter cake is dissolved in 120 ml 2 mol/L hydrochloric acid aqueous solution, cooling to 2 - 8 C stirring crystallization 2h, filtering, drying, to obtain 7.0g white solid, yield 32.6%, HPLC purity 96.5%.

Reference： [1]Patent: CN106333952,2017,A .Location in patent: Paragraph 0049-0052

29
[ 73742-45-7 ]
[ 7544-75-4 ]
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.7%	With sodium ethanolate; In N,N-dimethyl-formamide; at 20℃; for 18h;	To a suspension of 5-chloro-6-(chloromethyl)pyrimidine-2,4(lH,3H)-dione (25 g, 0.1282 mole) in Ν,Ν-dimethyl formamide (250 ml), 2-amino-l-pyrroline hydrochloride (30.91 g, 0.2564 mole) and sodium ethoxide (26.17 g, 0.3846 mole) was added. The reaction was stirred at room temperature for 18 hours. The progress of reaction was monitored by TLC. After completion of reaction the solid was filtered to give a pale brown cake. 75 ml of water was added to the wet cake and pH=7 was adjusted with acetic acid. Solid was filtered and the wet cake obtained was dissolved in 125 ml of aqueous hydrochloric acid solution at 60C, to which activated carbon was added and stirred for 30 minute at 60C. The mass was filtered on hyflo bed and washed with water (25 ml). Filtrate obtained was cooled to 0-10C and acetone (750 ml) was added drop wise under stirring. The reaction mass was stirred for 2 hours at 0-10C. The solid was filtered and washed with mixture of acetone: water (6: 1) (5 ml X 2) which was further dried at 50C for 10 hours to give white product (18.5 g). Yield: 51.70%

Reference： [1]Patent: WO2019/2407,2019,A1 .Location in patent: Page/Page column 44

30
[ 7544-75-4 ]
[ 136850-48-1 ]
(±)-aglaroxin C [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 1312 - 1323

31
[ 7544-75-4 ]
methyl (2S,3R,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
(6S,6aR,11bS)-11b-hydroxy-9,11-dimethoxy-6a-(4-methoxyphenyl)-6-phenyl-1,2,3,6,6a,11b-hexahydro-5H-benzofuro[2',3':4,5]cyclopenta[1,2-d]pyrrolo[1,2-a]pyrimidin-5-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 1312 - 1323

32
7-(bromomethyl)-2-(3,5-dimethoxybenzyl)-5-(4-fluoro-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
[ 7544-75-4 ]
2-(3,5-dimethoxybenzyl)-5-(4-fluoro-2-methylphenyl)-7-((2-iminopyrrolidin-1-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 656 - 675

33
[ 7544-75-4 ]
[ 136850-48-1 ]
(±)-aglaroxin C [ No CAS ]
[ 117828-45-2 ]

Reference： [1]Patent: US2020/123170,2020,A1 .Location in patent: Paragraph 0023

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[ 7544-75-4 ]

Amines

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[ 7544-75-4 ]

Pyrrolines

[ 872-32-2 ]

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Ghs Precautionary Statements

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Response
Code	Phrase
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P304	IF INHALED:
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P315	Get immediate medical advice/attention.
P320
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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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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.
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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.
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Disposal
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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. 7544-75-4 ] {[proInfo.proName]}

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[ 7544-75-4 ] Synthesis Path-Upstream 1~2

[ 7544-75-4 ] Synthesis Path-Downstream 1~33

Related Functional Groups of [ 7544-75-4 ]

Amines

Related Parent Nucleus of [ 7544-75-4 ]

Pyrrolines

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[ 7544-75-4 ]

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[ 7544-75-4 ]