Aniline → HCID 46830850, compound

HRID 1182666Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=3)=[CH:22][CH:21]=2)[CH:4]=[C:5]2[C:10]=1[N:9]1[C@H:11]3[CH2:16][CH2:15][CH2:14][C@H:12]3[N:13]=[C:8]1[N:7]([CH3:17])[C:6]2=[O:18].ClC(Cl)(Cl)C(O)=O.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl>[CH3:17][N:7]1[C:6](=[O:18])[C:5]2=[CH:4][N:3]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=4)=[CH:22][CH:21]=3)[C:2]([NH:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[C:10]2[N:9]2[C@H:11]3[CH2:16][CH2:15][CH2:14][C@H:12]3[N:13]=[C:8]12

Participants

Conditions

Temperature: 100 °C

Procedure

Crude (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-1-chloro-5-methyl-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one (approx. 0.03 mmol) is dissolved in anhydrous CH2Cl2, and then trichloroacetic acid (5.2 mg, 0.03 mmol) is added, followed by aniline (5.8 uL, 0.06 mmol). The reaction mixture is heated in a Biotage microwave instrument at 100° C. for 2 hours. The mixture is purified by a semi-preparative HPLC to give 2.2 mg of product as solids. MS (ESI) m/z 507.2 [M+H]+.

Workup

customThe mixture is purified by a semi-preparative HPLC

Sources & evidence

ORD record: ord-44f52011ce894f968b2a8a979f922d45
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664207B2

Reaction notes

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