HCID 86622699, compound → HCID 67007514, compound

HRID 729635Notes

Reaction equation

OC(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[CH:19][C:18]([C:21]([NH:23][C@H:24]3[C@@H:28]([OH:29])[CH2:27][NH:26][CH2:25]3)=[O:22])=[CH:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1.Cl[C:31]1[CH:36]=[C:35]([C:37]([C:39]2[S:40][CH:41]=[CH:42][N:43]=2)=[O:38])[CH:34]=[CH:33][N:32]=1>C(O)CCC>[F:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[CH:19][C:18]([C:21]([NH:23][C@H:24]3[C@@H:28]([OH:29])[CH2:27][N:26]([C:31]4[CH:36]=[C:35]([C:37]([C:39]5[S:40][CH:41]=[CH:42][N:43]=5)=[O:38])[CH:34]=[CH:33][N:32]=4)[CH2:25]3)=[O:22])=[CH:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a vial was added cis-2-(3-fluorophenyl)-N-(4-hydroxypyrrolidin-3-yl)pyrimidine-5-carboxamide-TFA salt (50 mg, 0.12 mmol), n-butanol (0.2 mL), TEA (0.016 mL, 0.12 mmol) and (2-chloropyridin-4-yl)(thiazol-2-yl)methanone (40.5 mg, 0.18 mmoL). The reaction mixture was heated to 85° C. for 4 hrs and then cooled to rt. The residue mixture was purified by RP-HPLC to give the desired product, cis-2-(3-fluorophenyl)-N-(4-hydroxy-1-(4-(thiazole-2-carbonyl)pyridin-2-yl)pyrrolidin-3-yl)pyrimidine-5-carboxamide (20 mg, 34%). HRMS (M+H) expected=491.1302, observed=491.1357.

Workup

temperaturecooled to rt
customThe residue mixture was purified by RP-HPLC

Sources & evidence

ORD record: ord-9ca0074d7e444ce4941cae4dcb187bec
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582643B2

Reaction notes

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