2-Aminothiazole → tert-butyl 4-(3-(imidazo[2,1-b]thiazol-6-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

HRID 2206338Notes

Reaction equation

HRID 2206338 reaction equation
Br[CH2:2][C:3]([C:5]1[C:28](=[O:29])[O:27][C:8]2=[N:9][C:10]([N:13]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]3)=[CH:11][CH:12]=[C:7]2[CH:6]=1)=O.[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>CCO>[S:32]1[CH:33]=[CH:34][N:35]2[CH:2]=[C:3]([C:5]3[C:28](=[O:29])[O:27][C:8]4=[N:9][C:10]([N:13]5[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:15][CH2:14]5)=[CH:11][CH:12]=[C:7]4[CH:6]=3)[N:30]=[C:31]12

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 89793974tert-butyl 4-(3-(2-bromoacetyl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 89793975tert-butyl 4-(3-(imidazo[2,1-b]thiazol-6-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylateYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-(3-(2-bromoacetyl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate (132 mg, 0.28 mmol) in 5 mL of EtOH was treated with 2-aminothiazole (34.1 mg, 0.34 mmol) at room temperature. The solution was refluxed for 16 hours and concentrated under vacuum. The residue was purified on silica gel to provide tert-butyl 4-(3-(imidazo[2,1-b]thiazol-6-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate (64.3 mg, 49%). MS m/z 468 [M+H]+.

Workup

  1. temperatureThe solution was refluxed for 16 hours
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-0bee919acf2d46b6883ff9ef6078b391
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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