Azidotrimethylsilane → HCID 178513754, compound

HRID 1971004Notes

Reaction equation

HRID 1971004 reaction equation
[CH:1]1([C@@H:4]([NH:9][C:10]2[C:22]3[C:21]4[CH:20]=[CH:19][C:18]([C:23]#[CH:24])=[CH:17][C:16]=4[NH:15][C:14]=3[C:13]([C:25]([NH2:27])=[O:26])=[CH:12][N:11]=2)[C:5]([F:8])([F:7])[F:6])[CH2:3][CH2:2]1.[Si]([N:32]=[N+:33]=[N-:34])(C)(C)C>>[CH:1]1([C@@H:4]([NH:9][C:10]2[C:22]3[C:21]4[CH:20]=[CH:19][C:18]([C:23]5[N:32]=[N:33][NH:34][CH:24]=5)=[CH:17][C:16]=4[NH:15][C:14]=3[C:13]([C:25]([NH2:27])=[O:26])=[CH:12][N:11]=2)[C:5]([F:8])([F:6])[F:7])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 59543129HCID 59543129, compound

Product 1

HCID 178513754HCID 178513754, compound

Procedure

1-{[(1R)-1-Cyclopropyl-2,2,2-trifluoroethyl]amino}-7-ethynyl-5H-pyrido[4,3-b]indole-4-carboxamide (0.13 g, 0.36 mmol) in TMS-azide (4 mL, 30 mmol) was heated to 150° C. for 18 h, cooled to room temperature, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 11.73 (s, 1H); 8.50 (d, 1H); 8.48 (s, 1H); 8.30 (br s, 1H); 8.22 (s, 1H); 7.93 (br s, 1H); 7.72 (d, 1H); 7.26 (br s, 1H); 6.98 (d, 1H); 4.85 (m, 1H); 1.58 (m, 1H); 0.72 (m, 1H); 0.62 (m, 1H); 0.51 (m, 1H); 0.31 (m, 1H). LRMS (APCI) calc'd for (C19H16F3N7O) [M+H]+, 416.1. found 416.1.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-49586ab3f921482b90b38e4f090c3fb7
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

Loading…