2-Methyl-3-butyn-2-ol → HCID 86693441, compound

HRID 575393Notes

Reaction equation

HRID 575393 reaction equation
Br[C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]4[O:22][N:21]=[C:20]([CH:23]5[CH2:25][CH2:24]5)[N:19]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.[CH3:28][C:29]([OH:33])([CH3:32])[C:30]#[CH:31]>>[CH:23]1([C:20]2[N:19]=[C:18]([C:12]3[N:8]4[CH2:9][CH2:10][O:11][C:5]5[CH:4]=[C:3]([F:27])[C:2]([C:31]#[C:30][C:29]([OH:33])([CH3:32])[CH3:28])=[CH:26][C:6]=5[C:7]4=[N:14][C:13]=3[C:15]([NH2:17])=[O:16])[O:22][N:21]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 86693442HCID 86693442, compound

Product 1

HCID 86693441HCID 86693441, compoundYield 28.6%

Procedure

3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly according to General Procedure G with slight modifications. 10-bromo-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was reacted with 3-methyl-1-butyne-3-ol to afford 26 mg of the titled compound (28.6% yield). M+1=438.0. 1H NMR (400 MHz, DMSO-d6) δ 8.63 (d, J=8.3 Hz, 1H), 7.99 (br s, 1H), 7.52 (br s, 1H), 7.07 (d, J=10.5 Hz, 1H), 5.56 (s, 1H), 4.58-4.51 (m, 4H), 2.28-2.19 (m, 1H), 1.49 (s, 6H), 1.19-1.09 (m, 2H), 1.03-0.97 (m, 2H).

Workup

  1. custom3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly

Sources & evidence

ORD record
ord-3e52253756b64459a176106d7c9ba9a7
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…