HCID 66676749, compound → HCID 178428259, compound

HRID 421977Notes

Reaction equation

C([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([CH2:18][N:19]3[CH2:24][C@@H:23]4[CH2:25][C@H:20]3[CH2:21][N:22]4[C:26](=[O:35])[C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=3[F:34])[N:12]=2)=[CH:8][CH:7]=[N:6]1)(C)(C)C>C(O)=O>[Cl:33][C:29]1[C:28]([F:34])=[C:27]([CH:32]=[CH:31][CH:30]=1)[C:26]([N:22]1[CH2:21][C@@H:20]2[CH2:25][C@H:23]1[CH2:24][N:19]2[CH2:18][C:13]1[N:12]=[C:11]([NH:10][C:9]2[CH:8]=[CH:7][NH:6][N:5]=2)[CH:16]=[C:15]([CH3:17])[N:14]=1)=[O:35]

Participants

Conditions

Temperature: 100 °C

Procedure

101 mg of N-(1-tert-butyl-1H-pyrazol-5-yl)-2-(((1S,4S)-5-(3-chloro-2-fluorobenzoyl) -2,5-diazabicyclo[2.2.1]hept-2-yl)methyl)-6-methylpyrimidine-4-amine was dissolved in 1 ml of formic acid followed by stirring at 100° C. for 3 hours. The reaction solution was concentrated in vacuo, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate, water and saturated brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by a reversed phase preparative liquid chromatography to give the title compound.

Workup

concentrationThe reaction solution was concentrated in vacuo
additiondiluted with ethyl acetate
washwashed with saturated sodium bicarbonate, water and saturated brine
dry with materialThe resulting organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
customThe resulting residue was purified by a reversed phase preparative liquid chromatography

Sources & evidence

ORD record: ord-22652c3d0dea4e60b190df33a18eb2c2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101621B2

Reaction notes

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