HCID 69027424, compound → 4-[4-(5-Chloro-thiophen-2-yl)-benzyl]-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one

HRID 1433068Notes

Reaction equation

HRID 1433068 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[S:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:27][CH:26]=2)[CH2:20][C:19]1=[O:37])=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:36][C:33]1[S:32][C:31]([C:28]2[CH:27]=[CH:26][C:25]([CH2:24][N:21]3[CH2:22][CH2:23][N:18]([CH2:17][C:9]4[NH:8][C:16]5[CH:15]=[CH:14][N:13]=[CH:12][C:11]=5[CH:10]=4)[C:19](=[O:37])[CH2:20]3)=[CH:30][CH:29]=2)=[CH:35][CH:34]=1

Participants

3

Reactant 1

HCID 69027424HCID 69027424, compound

Product 1

HCID 670135884-[4-(5-Chloro-thiophen-2-yl)-benzyl]-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-oneYield 47.1%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

2-{4-[4-(5-Chloro-thiophen-2-yl)-benzyl]-2-oxo-piperazin-1-ylmethyl}-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.90 g, 0.17 mmol) is stirred in 30% TFA/CH2Cl2 (8 mL) for 1 h then concentrated to dryness and purified by RP-HPLC using 10-100% acetonitrile/0.1% TFA water as the eluent. The appropriate fractions are collected and lypholized to yield the title product as an amorphous white solid (0.44 mg, 0.08 mmol).

Workup

  1. concentrationthen concentrated to dryness
  2. custompurified by RP-HPLC
  3. customThe appropriate fractions are collected

Sources & evidence

ORD record
ord-159fa102396f4baaa4cc0eda14a4fa47
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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