Hydrochloric Acid → HCID 86711291, compound

HRID 336156Notes

Reaction equation

Cl.[NH2:2][C:3]1[C:8]2[C:9]([C:25]3[CH:26]=[N:27][C:28]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)=[C:10]3[CH2:16][CH2:15][C@H:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13][CH2:12][N:11]3[C:7]=2[N:6]=[CH:5][N:4]=1.[OH-].[Na+]>C(O)C>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[C:25]([C:9]2[C:8]3[C:3]([NH2:2])=[N:4][CH:5]=[N:6][C:7]=3[N:11]3[CH2:12][CH2:13][C@@H:14]([NH2:17])[CH2:15][CH2:16][C:10]=23)[CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5 N Hydrochloric acid (1 ml) was added to a solution of (S)-tert-butyl (4-amino-5-(quinolin-3-yl)-7,8,9,10-tetrahydro-6H-pyrimido[5′,4′:4,5]pyrrolo[1,2-a]azepin-8-yl)carbamate (436 mg) obtained in Step 8 in ethanol (4 ml) at room temperature. The mixture was stirred at 60° C. for 3 hours. After cooling, the reaction mixture was basified with a 5 N aqueous sodium hydroxide solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a light-yellow solid (320 mg).

Workup

temperatureAfter cooling
extractionfollowed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol)

Sources & evidence

ORD record: ord-5636be3021434e1c9141907c68452137
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889666B2

Reaction notes

Loading…