Acetic Acid → HCID 58382048, compound

HRID 1628086Notes

Reaction equation

HRID 1628086 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:31]=O)[N:12]3[C:17]4[CH:18]=[CH:19][N:20]([S:21]([C:24]5[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=5)(=[O:23])=[O:22])[C:16]=4[N:15]=[CH:14][C:13]=23)=[CH:5][CH:4]=1.CC(O)=O.[CH:37]1([NH2:40])[CH2:39][CH2:38]1.C([BH3-])#N>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:31][NH:40][CH:37]3[CH2:39][CH2:38]3)[N:12]3[C:17]4[CH:18]=[CH:19][N:20]([S:21]([C:24]5[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=5)(=[O:23])=[O:22])[C:16]=4[N:15]=[CH:14][C:13]=23)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 498716Cyano-borohydrideHCID 58382331HCID 58382331, compound

Product 1

HCID 58382048HCID 58382048, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(4-Methoxyphenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine-1-carbaldehyde (0.075 g, 0.17 mmol), AcOH (0.048 mL, 0.84 mmol), and cyclopropanamine (0.026 mL, 0.37 mmol) were added in DCE (1.68 mL). The mixture was stirred at rt for 30 min. MP-Cyanoborohydride (0.23 g, 0.50 mmol, 2.15 mmol/g, Biotage™) was added in one portion. The mixture was stirred at 25° C. for 72 h. The mixture was purified directly by flash chromatography (40 g silica gel column, MeOH/DCM 0% to 10%) to give N-((3-(4-methoxyphenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methyl)cyclopropanamine (0.050 g, 61%): LC/MS (Table 2, Method c) Rt=1.49 min; MS m/z: 488 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 25° C. for 72 h
  2. customThe mixture was purified directly by flash chromatography (40 g silica gel column, MeOH/DCM 0% to 10%)

Sources & evidence

ORD record
ord-1be00e25f4f749179e21413477a15ca3
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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