Ammonia → HCID 86693499, compound

HRID 575441Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]3[CH2:21][CH:12]([C:13]4[CH:18]=[C:17]([F:19])[C:16]([I:20])=[CH:15][C:14]=4[C:8]=2[N:7]=[C:6]1[C:22]([O:24]CC)=O)[CH2:11]3.[NH3:31]>>[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]3[CH2:21][CH:12]([C:13]4[CH:18]=[C:17]([F:19])[C:16]([I:20])=[CH:15][C:14]=4[C:8]=2[N:7]=[C:6]1[C:22]([NH2:31])=[O:24])[CH2:11]3

Participants

Reactant 2

HCID 222Ammonia

HCID 86693500HCID 86693500, compound

Product 1

HCID 86693499HCID 86693499, compoundYield 100%

Conditions

Temperature: 44 °C

Procedure

A pressure tube containing a solution of ethyl 3-(2-chlorobenzyl)-8-fluoro-9-iodo-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (89 mg, 0.17 mmol) in methanolic ammonia (5 mL of 7.0M ammonia in methanol) was warmed to 44° C. for 36 hr. Evaporation of the reaction mixture furnished the title compound (86 mg, 0.17 mmol, 100%) as a colorless solid: 1H NMR (500 MHz, CDCl3) δ 1.63 (d, J=11.35 Hz, 1H), 2.81 (dd, J=7.72, 3.00 Hz, 2H), 3.14-3.23 (m, 1H), 3.54 (td, J=8.43, 4.26 Hz, 1H), 5.39 (br. s, 1H), 5.92 (s, 1H), 6.42 (d, J=7.57 Hz, 1H), 6.82 (d, J=8.83 Hz, 1H), 7.09-7.15 (m, 1H), 7.17-7.23 (m, 1H), 7.41 (d, J=0.95 Hz, 1H), 7.44-7.66 (m, 1H), 8.83 (d, J=6.94 Hz, 1H); M+1=530/532.

Workup

customEvaporation of the reaction mixture

Sources & evidence

ORD record: ord-934af7b9b63d4d4598d4bb8142f63237
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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