Ammonia → 8-fluoro-9-iodo-3((1-methyl-1H-pyrazol-5-yl)methyl)-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamide

HRID 575439Notes

Reaction equation

[F:1][C:2]1[C:28]([I:29])=[CH:27][C:5]2[C:6]3[N:10]=[C:9]([C:11]([O:13]CC)=O)[N:8]([CH2:16][C:17]4[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=4)[C:7]=3[CH:23]3[CH2:26][CH:25]([C:4]=2[CH:3]=1)[CH2:24]3.[NH3:30]>>[F:1][C:2]1[C:28]([I:29])=[CH:27][C:5]2[C:6]3[N:10]=[C:9]([C:11]([NH2:30])=[O:13])[N:8]([CH2:16][C:17]4[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=4)[C:7]=3[CH:23]3[CH2:26][CH:25]([C:4]=2[CH:3]=1)[CH2:24]3

Participants

Reactant 2

HCID 222Ammonia

HCID 86693496ethyl 8-fluoro-9-iodo-3((1-methyl-1H-pyrazol-5-yl)methyl)-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate

Product 1

HCID 866934978-fluoro-9-iodo-3((1-methyl-1H-pyrazol-5-yl)methyl)-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamideYield 93%

Conditions

Temperature: 44 °C

Procedure

A pressure tube containing a solution of ethyl 8-fluoro-9-iodo-3((1-methyl-1H-pyrazol-5-yl)methyl)-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (77 mg, 0.15 mmol) in methanolic ammonia (5 mL of 7.0M ammonia in methanol) was warmed to 44° C. for 48 hr. Evaporation of the reaction mixture furnished the title compound (67 mg, 0.14 mmol, 93%) as a colorless solid: 1H NMR (500 MHz, d4-methanol) δ 1.65 (d, J=11.35 Hz, 2H), 2.93-3.02 (m, 2H), 3.47-3.53 (m, 1H), 3.64 (td, J=8.04, 4.10 Hz, 1H), 3.89 (s, 3H), 5.61 (d, J=1.89 Hz, 1H), 5.88 (s, 2H), 6.93 (d, J=8.83 Hz, 1H), 7.30 (d, J=1.89 Hz, 1H), 8.79 (d, J=6.94 Hz, 1H); M+H=478.

Workup

customEvaporation of the reaction mixture

Sources & evidence

ORD record: ord-f3e6bf781e7a4df9926ae41cfe2aca77
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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