Ammonia → HCID 86693501, compound

HRID 575442Notes

Reaction equation

[F:1][CH:2]([F:25])[N:3]1[C:7]2[CH:8]3[CH2:19][CH:10]([C:11]4[CH:16]=[C:15]([F:17])[C:14]([I:18])=[CH:13][C:12]=4[C:6]=2[N:5]=[C:4]1[C:20]([O:22]CC)=O)[CH2:9]3.[NH3:26]>>[F:25][CH:2]([F:1])[N:3]1[C:7]2[CH:8]3[CH2:19][CH:10]([C:11]4[CH:16]=[C:15]([F:17])[C:14]([I:18])=[CH:13][C:12]=4[C:6]=2[N:5]=[C:4]1[C:20]([NH2:26])=[O:22])[CH2:9]3

Participants

Reactant 2

HCID 222Ammonia

HCID 86693502HCID 86693502, compound

Product 1

HCID 86693501HCID 86693501, compoundYield 80%

Conditions

Temperature: 44 °C

Procedure

A pressure tube containing a solution of ethyl 3-(difluoromethyl)-8-fluoro-9-iodo-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (11 mg, at 52% purity LCMS-UV215) 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 (12 mg at 80% purity LCMS-UV215) as a colorless solid which was carried through to the next synthetic step without purification: 1H NMR (500 MHz, CDCl3) δ 1.70-1.16 (m, 2H), 2.95-3.02 (m, 2H), 3.59 (td, J=8.2, 3.5 Hz, 1H), 3.86-3.91 (m, 1H), 5.58 (br. s, 1H), 6.86 (d, J=8.6 Hz, 1H), 7.40 (br. s, 1H), 8.71 (d, J=6.6 Hz, 1H), 8.75 (t, J=58.6 Hz, 1H); M+H=434.

Workup

customEvaporation of the reaction mixture

Sources & evidence

ORD record: ord-60d9c5c8d0204329acf36a6ac21156a8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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