Piperazine → HCID 24737756, compound

HRID 1990713Notes

Reaction equation

HRID 1990713 reaction equation
C(O[C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([Cl:14])=[CH:13][C:8]=2[CH:7]=1)=[O:5])C.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[Cl:14][C:12]1[S:11][C:9]2[NH:10][C:6]([C:4]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:5])=[CH:7][C:8]=2[CH:13]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 116010652-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester

Product 1

HCID 24737756HCID 24737756, compoundYield 35%

Procedure

2-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester (102 mg, 0.45 mmol) was hydrolyzed (Procedure B) and then coupled with piperazine (Procedure D) to provide the title compound (42 mg, 35% for two steps) as an off-white solid. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.15. MS (electrospray): exact mass calculated for C11H12ClN3OS, 269.04; m/z found, 270.1 [M+H]+. 1H NMR (CDCl3, 400 MHz): 10.5 (br s, 1H), 6.87 (s, 1H), 6.61 (s, 1H), 3.87 (t, J=4.8 Hz, 4H), 2.96 (t, J=5.2 Hz, 4H).

Sources & evidence

ORD record
ord-d98851c2653f4b1a84983f6348d71f99
Source dataset
uspto-grants-2010_01
Patent number
US07645758B2

Reaction notes

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