1-Bromo-3-methylbutane → (S)-N-(1-(1-isopentyl-1H-imidazol-2-yl)-2-phenylethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

HRID 1506619Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]([NH:14][C:15](=[O:30])[CH2:16][N:17]1[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[C:19]([C:26]([F:29])([F:28])[F:27])=[N:18]1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:32]([N:3]1[CH:4]=[CH:5][N:1]=[C:2]1[C@@H:6]([NH:14][C:15](=[O:30])[CH2:16][N:17]1[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[C:19]([C:26]([F:27])([F:28])[F:29])=[N:18]1)[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:33][CH:34]([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-N-(1-(1H-imidazol-2-yl)-2-phenylethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide (42 mg, 0.1 mmol) and 1-bromo-3-methylbutane (24 μL, 0.2 mmol) were combined in DMF (0.6 mL) and treated with K2CO3 (21 mg, 0.15 mmol) and TBAI (4 mg). The reaction was heated to 90° C. and stirred for 15 h. The reaction was purified by RP HPLC to provide the title compound: 1H NMR (400 MHz, DMSO-d6) δ 7.23 (q, 7.5 Hz, 3H), 7.16-7.09 (m, 2H), 5.24 (m, 1H), 4.75 (s, 2H), 3.83 (m, 3H), 3.22 (d, 1H), 2.35 (m, 2H), 1.63 (m, 5H), 1.40 (m, 2H), 0.77 (t, 6H). MS (m/z) 488.5 [M+H]+.

Workup

customThe reaction was purified by RP HPLC

Sources & evidence

ORD record: ord-d02ecbc86b584d8e8c92096a7f7cb5d1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09220710B2

Reaction notes

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