Sodium hydride → HCID 10221762, compound

HRID 1241381Notes

Reaction equation

HRID 1241381 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)[CH:3]=1.[H-].[Na+].Cl[C:24]1[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=1>>[C:29]([C:26]1[S:25][C:24]([NH:1][C:2]2[N:7]=[CH:6][N:5]=[C:4]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]3)[CH:3]=2)=[N:28][CH:27]=1)#[N:30]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934625HCID 21934625, compound

Product 1

HCID 10221762HCID 10221762, compound

Procedure

2-[4-(6-aminopyrimidin-4-yl)piperazin-1-yl]-N-isopropylacetamide 13-2 (0.45 g, 1.62 mmol), sodium hydride (0.13 g, 3.25 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.235 g, 1.62 mmol) were treated as in Scheme 4 above. The product was purified on a C18 preparative column and isolated via lyophilization. Hi-Res MS: calc: 387.1710 found: 387.1691. 1NMR (DMSO): 8.51 ppm (s, 1H); 8.47 ppm (s, 1H); 8.28 ppm (s, 1H); 6.30 ppm (s, 1H); 4.35 ppm (m, 2H); 3.91 ppm (m, 4H); 3.39 ppm (m, 2H); 3.18 ppm (m, 2H); 1.11 ppm (d, 6H).

Workup

  1. customThe product was purified on a C18 preparative column
  2. customisolated via lyophilization

Sources & evidence

ORD record
ord-894561ca51684732ab7bee78e565c2b4
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…