Sodium hydride → HCID 58714276, compound

HRID 1241386Notes

Reaction equation

HRID 1241386 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][C@@H:12]3[CH2:14][C@H:9]2[CH2:10][N:11]3C(OC(C)(C)C)=O)[CH:3]=1.[H-].[Na+].Cl[C:25]1[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=1>>[C@H:9]12[CH2:14][C@H:12]([NH:11][CH2:10]1)[CH2:13][N:8]2[C:4]1[N:5]=[CH:6][N:7]=[C:2]([NH:1][C:25]2[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 86585955HCID 86585955, compound

Product 1

HCID 58714276HCID 58714276, compound

Procedure

Tert-butyl (1S,4S)-5-(6-aminopyrimidin-4-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 16-2 (0.324 g, 1.11 mmol), sodium hydride (0.089 g, 2.22 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.161 g, 1.11 mmol) were treated as in Scheme 4 above. The product was purified on a C18 preparative column after treating the crude product with trifluoroacetic acid and then converted to a free base form after isolation via lyophilization. Hi-Res MS: calc: 300.1026 found: 300.1039. 1NMR (DMSO): 8.36 ppm (s, 1H); 8.23 ppm (s, 1H); 5.88 ppm (s, 1H); 4.90 ppm (s, 1H); 3.77 ppm (s, 1H); 3.41 ppm (s, 1H); 3.32 ppm (m, 2H); 2.93 ppm (d, 1H); 2.79 ppm (d, 1H); 1.78 ppm (m, 1H); 1.69 ppm (m, 1H).

Workup

  1. customThe product was purified on a C18 preparative column
  2. additionafter treating the crude product with trifluoroacetic acid

Sources & evidence

ORD record
ord-50dd1cfd82cb4d8ba8f12447072c4dfd
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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