Ammonia → 8-Fluoro-9-iodo-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamide

HRID 575433Notes

Reaction equation

HRID 575433 reaction equation
[F:1][C:2]1[C:21]([I:22])=[CH:20][C:5]2[C:6]3[N:10]=[C:9]([C:11]([O:13]CC)=O)[NH:8][C:7]=3[CH:16]3[CH2:19][CH:18]([C:4]=2[CH:3]=1)[CH2:17]3.[NH3:23]>CO>[F:1][C:2]1[C:21]([I:22])=[CH:20][C:5]2[C:6]3[N:10]=[C:9]([C:11]([NH2:23])=[O:13])[NH:8][C:7]=3[CH:16]3[CH2:17][CH:18]([C:4]=2[CH:3]=1)[CH2:19]3

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 86693491Ethyl 8-fluoro-9-iodo-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate

Product 1

HCID 866934908-Fluoro-9-iodo-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 8-fluoro-9-iodo-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (302 mg at 69% purity) in methanolic ammonia (7 mL of a 7.0M solution of ammonia in methanol, 49.0 mmol) was warmed to 44° C. for 72 hr in a pressure tube. After cooling to room temperature, the precipitous solution was evaporated to dryness in vacuo. The residue was re-suspended in methanol (1 mL) and the solid collected by filtration to furnish the title compound (155 mg, 0.40 mmol, 78%) as an off-white powder: 1H NMR (500 MHz, d6-DMSO) δ 1.47-1.49 (m, 2H), 2.83-2.91 (m, 2H), 3.40-3.44 (m, 1H), 3.60-3.68 (m, 1H), 7.10 (d, J=9.2 Hz, 1H), 7.42 (br. s, 1H), 7.82 (br, s, 1H), 8.64 (d, J=6.9 Hz, 1H), 13.08 (br. s, 1H); M+H=384

Workup

  1. customthe precipitous solution was evaporated to dryness in vacuo
  2. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-c85350f6f7e84112886a10443fa70622
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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