2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 86713960, compound

HRID 522068Notes

Reaction equation

HRID 522068 reaction equation
Br[C:2]1[S:3][C:4]([NH:32]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:31])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:30])[C:13]=2[C@@H:14]2[CH2:20][CH2:19][C@@H:18]([NH:21]C(OC(C)(C)C)=O)[C@H:17]([F:29])[CH2:16][O:15]2)[N:6]=1.[C:40]1(B2OC(C)(C)C(C)(C)O2)[CH2:44][CH2:43][CH2:42][CH:41]=1>>[NH2:32][C:4]1[S:3][C:2]([C:40]2[CH2:44][CH2:43][CH2:42][CH:41]=2)=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH3:30])[C:13]=1[C@@H:14]1[CH2:20][CH2:19][C@@H:18]([NH2:21])[C@H:17]([F:29])[CH2:16][O:15]1)=[O:31]

Participants

3

Reactant 2

HCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86713840tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6S)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate2×

Product 1

HCID 86713960HCID 86713960, compound

Procedure

Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6S)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 95), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with 2-(cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane gave 333. 1H NMR (400 MHz, DMSO-d6) δ 9.09 (s, 1H), 7.85 (s, 1H), 7.34 (s, 2H), 6.20-6.15 (m, 1H), 4.80 (dd, J=10.4, 3.7 Hz, 1H), 4.50-4.29 (m, 1H), 4.27-4.16 (m, 1H), 4.12-3.95 (m, 1H), 3.74 (s, 3H), 2.79-2.69 (m, 2H), 2.07-1.99 (m, 1H), 1.97-1.86 (m, 2H), 1.81-1.66 (m, 4H). LCMS (ES+) m/z 421 (M+1).

Sources & evidence

ORD record
ord-a29ab7ec3b264c1bacd6da3ea9019071
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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