Dimethylformamide → HCID 59239240, compound

HRID 1698042Notes

Reaction equation

HRID 1698042 reaction equation
[C:1]([CH2:3][CH:4]1[C:9]2[N:10]=[C:11]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)[N:12]=[C:13]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])[C:8]=2[CH2:7][CH2:6][NH:5]1)#[N:2].CN(C)C=O.C(N(CC)C(C)C)(C)C.[C:47](Cl)(=[O:49])[CH3:48]>>[C:47]([N:5]1[CH2:6][CH2:7][C:8]2[C:13]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])=[N:12][C:11]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)=[N:10][C:9]=2[CH:4]1[CH2:3][C:1]#[N:2])(=[O:49])[CH3:48]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67175716HCID 67175716, compound

Product 1

HCID 59239240HCID 59239240, compound

Procedure

1-(4-(8-(Cyanomethyl)-4-((S)-3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (0.100 g, 0.230 mmol) in dry N,N-Dimethylformamide (1.00 mL, 12.9 mmol) was added N,N-Diisopropylethylamine (0.120 mL, 0.689 mmol) followed by Acetyl chloride (0.0246 mL, 0.346 mmol). The reaction mixture was stirred for 4 hours. The reaction mixture was concentrated and chromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane). LC/MS-m/z+478.5 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-5a1462e976f74387a6dface6459967ad
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

Loading…