1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 59618682, compound

HRID 1691470Notes

Reaction equation

HRID 1691470 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:6]=2[C:33]=1[Cl:34].[CH3:35][N:36]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[N:37]1>>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:7]2[C:6]3[C:33]([Cl:34])=[C:2]([C:39]4[CH:38]=[N:37][N:36]([CH3:35])[CH:40]=4)[CH:3]=[CH:4][C:5]=3[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:9]=3[CH2:8]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1)([CH3:31])([CH3:30])[CH3:32]

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 66901659HCID 66901659, compound2×

Product 1

HCID 59618682HCID 59618682, compound

Procedure

The title compound was prepared from 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-7-chloro-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 64) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole according to the procedure of Example 495. Racemic mixture: LC/MS: m/e 576.1 (M+H)+; 1H NMR (500 MHz, CD3OD): δ 8.05 (1H, s), 7.80 (1H, s), 7.58 (1H, d), 7.41 (2H, d), 7.10 (3H, m), 7.05 (1H, d), 7.00-7.10 (2H, d), 5.19 (1H, d), 5.55 (1H, d), 3.96 (3H, s), 1.26 (9H, s). The racemic mixture was separated on a Chiracel OD-H column eluting with 20% EtOH in hexanes at 8.0 mL/min. The faster eluting enantiomer E1 had a retention time of 40 min. The slower eluting enantiomer E2 had a retention time of 50 min.

Workup

  1. customThe racemic mixture was separated on a Chiracel OD-H column
  2. washeluting with 20% EtOH in hexanes at 8.0 mL/min
  3. washThe faster eluting enantiomer E1
  4. washThe slower eluting enantiomer E2

Sources & evidence

ORD record
ord-05a1167660514ecf94e3f5a34ce15116
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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