HCID 70655036, compound → HCID 86713966, compound

HRID 522074Notes

Reaction equation

HRID 522074 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.[F:32][C:33]1[CH:38]=[C:37]([C:39]2([O:43][CH3:44])[CH2:42][O:41][CH2:40]2)[CH:36]=[C:35]([F:45])[C:34]=1B1OC(C)(C)C(C)(C)O1>>[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:34]3[C:35]([F:45])=[CH:36][C:37]([C:39]4([O:43][CH3:44])[CH2:40][O:41][CH2:42]4)=[CH:38][C:33]=3[F:32])[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 70655036HCID 70655036, compoundHCID 86713845tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate2×

Product 1

HCID 86713966HCID 86713966, 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 2-(2,6-difluoro-4-(3-methoxyoxetan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (US2012/225062) gave 339. 1H NMR (500 MHz, DMSO-d6) δ 9.91 (s, 1H), 8.65 (s, 1H), 7.88 (s, 1H), 7.46-7.44 (m, 2H), 4.82-4.79 (m, 5H), 4.37-3.93 (m, 3H), 3.78 (s, 3H), 3.24-3.17 (m, 1H), 3.12 (s, 3H), 2.07-1.67 (m, 4H). LCMS (ES+) m/z 538 (M+1).

Sources & evidence

ORD record
ord-69623cff923d4ace917b51c8d2e73600
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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