Ammonia → HCID 90412858, compound

HRID 1526642Notes

Reaction equation

C([NH:9][C:10]1[O:11][C@@H:12]2[C@H:14]([C@@:15]([C:18]3[CH:19]=[C:20]([NH:25][C:26]([C:28]4[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=4)=[O:27])[CH:21]=[CH:22][C:23]=3[F:24])([CH3:17])[N:16]=1)[CH2:13]2)(=O)C1C=CC=CC=1.N>>[NH2:9][C:10]1[O:11][C@@H:12]2[C@H:14]([C@@:15]([C:18]3[CH:19]=[C:20]([NH:25][C:26]([C:28]4[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=4)=[O:27])[CH:21]=[CH:22][C:23]=3[F:24])([CH3:17])[N:16]=1)[CH2:13]2

Participants

Reactant 2

HCID 222Ammonia

HCID 90413812HCID 90413812, compound

Product 1

HCID 90412858HCID 90412858, compoundYield 48.4%

Conditions

Temperature: 80 °C

Procedure

A sealed vial was charged with N-(3-((1S,5R,6S)-3-benzamido-5-methyl-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide (319a, 0.341 g, 0.717 mmol) and ammonia (2.0M solution in methanol; 7.17 ml, 14.34 mmol, Aldrich). The reaction mixture was heated to 80° C. for 24 h. The reaction was concentrated under reduced pressure and purified via silica gel flash chromatography using a gradient of 0-10% (2M ammonia in MeOH)/DCM to afford the title compound as a white solid. (0.129 g, 0.347 mmol, 48.4% yield).

Workup

concentrationThe reaction was concentrated under reduced pressure
custompurified via silica gel flash chromatography

Sources & evidence

ORD record: ord-2426a269c25d4dc78ec6e5a64a2d4b4e
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085576B2

Reaction notes

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