2-Fluoro-5-methylbenzeneboronic acid → HCID 73603035, compound

HRID 1915853Notes

Reaction equation

HRID 1915853 reaction equation
Br[C:2]1[S:3][C:4]([NH:34]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:33])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:29][CH:30]([F:32])[F:31])[C:13]=2[N:14]2[CH2:20][CH2:19][CH2:18][C@@H:17]([N:21]([CH3:28])C(=O)C(F)(F)F)[CH2:16][CH2:15]2)[N:6]=1.[F:42][C:43]1[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][C:44]=1B(O)O>>[NH2:34][C:4]1[S:3][C:2]([C:44]2[CH:45]=[C:46]([CH3:49])[CH:47]=[CH:48][C:43]=2[F:42])=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH2:29][CH:30]([F:31])[F:32])[C:13]=1[N:14]1[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21][CH3:28])[CH2:16][CH2:15]1)=[O:33]

Participants

3

Reactant 2

HCID 103518842-Fluoro-5-methylbenzeneboronic acidHCID 86679966HCID 86679966, compound

Product 1

HCID 73603035HCID 73603035, compound

Procedure

Following the procedure for Example 108, (R)-tert-butyl 2-bromo-4-(1-(2,2-difluoroethyl)-5-(4-(2,2,2-trifluoro-N-methylacetamido)azepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate (80 mg, 0.12 mmol) and 2-fluoro-5-methylbenzeneboronic acid (30 mg, 0.20 mmol) were reacted to give 119 as the mono formate salt as a pale pink solid (11 mg, 19% over two steps). 1H NMR (400 MHz, d4-MeOD) δ 8.56 (s, 1H), 8.08 (dd, J=7.3, 2.2 Hz, 1H), 7.60 (s, 1H), 7.26-7.20 (m, 1H), 7.12 (dd, J=11.4, 8.4 Hz, 1H), 6.41-6.08 (m, 1H), 4.54-4.43 (m, 2H), 3.40-3.33 (m, 3H), 3.32-3.24 (m, 2H), 2.64 (s, 3H), 2.41 (s, 3H), 2.33-1.94 (m, 3H), 1.91-1.76 (m, 3H). LCMS (ES+) m/z 508 (M+1).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-59bfc1617d3e487fbe969e3b9d8bda48
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

Loading…