Ammonia → HCID 86693485, compound

HRID 575429Notes

Reaction equation

HRID 575429 reaction equation
[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:19]3[CH2:20][CH:17]([CH2:18]3)[C:8]3[NH:9][C:10]([C:12]([O:14]CC)=O)=[N:11][C:7]=3[C:6]=2[CH:21]=1.[NH3:23]>CO>[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:19]3[CH2:20][CH:17]([CH2:18]3)[C:8]3[NH:9][C:10]([C:12]([NH2:23])=[O:14])=[N:11][C:7]=3[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 86693486HCID 86693486, compound

Product 1

HCID 86693485HCID 86693485, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 9-bromo-8-fluoro-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (80 mg, 0.22 mmol) in methanolic ammonia (10 mL of a 7M ammonia solution in methanol) was warmed to 40° C. for 3d in a pressure tube. Evaporation of the reaction mixture in vacuo furnished the title compound (77 mg, 0.22 mmol, 100%) as a colorless solid: 1H NMR (500 MHz, d4-methanol) δ 1.62-1.69 (m, 2H), 2.92-3.01 (m, 2H), 3.45-3.50 (m, 1H), 3.65-3.72 (m, 1H), 6.97-7.02 (m, 1H), 8.42-8.50 (m, 1H); M+1=336/338.

Workup

  1. customEvaporation of the reaction mixture in vacuo

Sources & evidence

ORD record
ord-6352f02130d94d8ab151b4522f7c0fbe
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…