tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate → HCID 90072637, compound

HRID 522040Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:31])[C:14]=2[C@H:15]2[O:21][CH2:20][C@@H:19]([F:22])[C@H:18]([NH:23]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[O:8])[N:6]=1.[CH:32]1([CH:35]([C:37]2[CH:42]=[C:41]([F:43])[C:40](B3OC(C)(C)C(C)(C)O3)=[C:39]([F:53])[CH:38]=2)[OH:36])[CH2:34][CH2:33]1>>[NH2:23][C@H:18]1[C@H:19]([F:22])[CH2:20][O:21][C@H:15]([C:14]2[N:13]([CH3:31])[N:12]=[CH:11][C:10]=2[NH:9][C:7]([C:5]2[N:6]=[C:2]([C:40]3[C:39]([F:53])=[CH:38][C:37]([CH:35]([CH:32]4[CH2:34][CH2:33]4)[OH:36])=[CH:42][C:41]=3[F:43])[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

Reactant 2

HCID 86713845tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate2×

HCID 86713869HCID 86713869, compound2×

Product 1

HCID 90072637HCID 90072637, compound

Procedure

Following the procedure for Example 101 starting from tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate (Intermediate 99), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with cyclopropyl(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (Intermediate 140) gave 275, which was isolated as a mixture of diastereomers. LCMS (ES+) m/z 522 (M+1).

Sources & evidence

ORD record: ord-d2e36f9d71914465a4c1893d6569f826
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328106B2

Reaction notes

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