Sodium hydride → HCID 21934619, compound

HRID 1241413Notes

Reaction equation

HRID 1241413 reaction equation
[N:1]1([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:26]1[S:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=1>>[N:1]1([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][N:19]=[C:18]([NH:22][C:26]4[S:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=4)[CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934699HCID 21934699, compound

Product 1

HCID 21934619HCID 21934619, compound

Procedure

42-3 (0.36 g, 1.18 mmol), sodium hydride (0.094 g, 2.35 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.17 g, 1.18 mmol) were treated as in Scheme 4 above. The reaction was cooled, quenched with methanol and water, evaporated to dryness and partitioned between methylene chloride, methanol and water. The organic layers were evaporated to dryness and purified on a C18 preparative hplc column and isolated via lyophilization to afford 42-4. Hi-Res MS: calc: 415.1659 found: 415.1638. 1H-NMR (CD3OD): 8.44(s, 1H); 8.01(s, 1H); 6.20(s, 1H); 4.36(s, 2H); 4.05(br s, 2H); 3.88(br s, 2H); 3.82(m, 2H); 3.76(m, 2H); 3.71(m, 2H); 3.56(m, 4H); 3.25(br s, 2H).

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with methanol and water
  3. customevaporated to dryness
  4. custompartitioned between methylene chloride, methanol and water
  5. customThe organic layers were evaporated to dryness
  6. custompurified on a C18 preparative hplc column
  7. customisolated via lyophilization
  8. customto afford 42-4

Sources & evidence

ORD record
ord-3f1b97eeff9243eea67563f4f63caff4
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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