Hydrochloric Acid → HCID 22396947, compound

HRID 1356335Notes

Reaction equation

HRID 1356335 reaction equation
[Br:1][C:2]1[C:10]2[N:9]([CH2:11][C:12]([NH:14][C:15]3[S:16][CH:17]=[C:18]([CH3:20])[N:19]=3)=[O:13])[C:8]3[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[ClH:33]>CCOC(C)=O.O1CCOCC1>[ClH:33].[Br:1][C:2]1[C:10]2[N:9]([CH2:11][C:12]([NH:14][C:15]3[S:16][CH:17]=[C:18]([CH3:20])[N:19]=3)=[O:13])[C:8]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22396948HCID 22396948, compound

Product 1

HCID 22396947HCID 22396947, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 7-bromo-6-{2-[(4-methyl-1,3-thiazol-2-yl)amino]-2-oxoethyl}-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.280 g, 0.52 mmol) was dissolved in EtOAc (15 mL). 4N HCl in dioxane (5 mL) was added and the reaction mixture was stirred at rt under N2. After 1 h, a white solid precipitated from the solution. The precipitate was collected by filtration. Pure 2-(7-bromo-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-N-(4-methyl-1,3-thiazol-2-yl)acetamide hydrochloride was obtained after recrystallization from 3:1 CH3OH:Et2O (20 mL), as a white solid (0.220 g) in 94% yield. 1H NMR (400 MHz, CD3OD) δ 2.4, 3.22-3.28, 3.49-3.59, 5.7-5.78, 6.88, 7.02, 7.35, 7.54; MS (ESI+) for C18H19BrN4OS m/z 420.8 (M+H)+.

Workup

  1. customa white solid precipitated from the solution
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ac9cc7b7b5e641fe939dc91d912af447
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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