Ethyl isocyanate → HCID 11238478, compound

HRID 2105525Notes

Reaction equation

HRID 2105525 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([N:23]4[C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[NH:25][C:24]4=[O:32])[CH2:19][CH2:18]3)=[CH:12][CH:11]=2)[C:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:6][C:3]=1[C:4]#[N:5].[CH2:39]([N:41]=[C:42]=[O:43])[CH3:40]>C1COCC1>[C:4]([C:3]1[C:2]([NH:1][C:42]([NH:41][CH2:39][CH3:40])=[O:43])=[N:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][N:17]3[CH2:18][CH2:19][CH:20]([N:23]4[C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[NH:25][C:24]4=[O:32])[CH2:21][CH2:22]3)=[CH:14][CH:15]=2)=[C:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=1)#[N:5]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 11249067HCID 11249067, compound

Product 1

HCID 11238478HCID 11238478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 2-amino-6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (6-3; 0.025 g, 0.05 mmol) and ethylisocyanate (0.007 mg, 0.100mmol) in THF (1 mL) was heated to 100 C for 0.5 h and concentrated. The residue was purified by silica gel chromatography (3-6% MeOH in CH2Cl2) to give the title compound (7-1). LRMS m/z (M+H) Calcd: 572.7, found: 572.2.

Workup

  1. temperaturewas heated to 100 C for 0.5 h
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (3-6% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-48905b2da53e4c7e90fb07bf08724dfa
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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