HCID 57976102, compound → HCID 178495809, compound

HRID 1865198Notes

Reaction equation

HRID 1865198 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[NH:20][C:19](=[O:21])[CH2:18][C:16]=3[N:17]=2)[CH2:7][CH2:6]1.[NH:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=1)=O>CCO.N>[NH:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=1)=[C:18]1[C:16]2[N:17]=[C:12]([NH:11][CH:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:10][CH2:9]3)[N:13]=[CH:14][C:15]=2[NH:20][C:19]1=[O:21]

Participants

5

Reactant 2

HCID 57976102HCID 57976102, compoundHCID 57976132HCID 57976132, compound

Product 1

HCID 178495809HCID 178495809, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

A mixture of crude 2-[1-(2-methoxy-ethyl)-piperidin-4-ylamino]-5,7-dihydro-pyrrolo[3,2-d]pyrimidin-6-one, TFA salts (8, 519 mgs, 0.71 mmol) and (1H-benzoimidazol-2-yl)-(3-chloro-phenyl)-methanone (9, 192 mgs, 0.75 mmol) was dissolved in EtOH saturated with ammonia (8.0 mls) and the mixture stirred at 90 C in a sealed reaction vessel overnight. The reaction mixture was concentrated in vacuo and purified by preparative HPLC to give 7-[(1H-Benzoimidazol-2-yl)-(3-chloro-phenyl)-methylene]-2-[1-(2-methoxy-ethyl)-piperidin-4-ylamino]-5,7-dihydro-pyrrolo[3,2-d]pyrimidin-6-one (10). LC/MS Calcd for [M+H]+ 530, found 530.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-39ab1a9ffd794213ad6124756113b962
Source dataset
uspto-grants-2009_12
Patent number
US07626031B2

Reaction notes

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