2-Methyl-3-butyn-2-ol → HCID 71715340, compound

HRID 575097Notes

Reaction equation

HRID 575097 reaction equation
Br[C:2]1[C:3]([F:31])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]4[N:22]([CH3:23])[N:21]=[C:20]([C:24]5[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=5)[N:19]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:30]=1.[CH3:32][C:33]([OH:37])([C:35]#[CH:36])[CH3:34]>>[F:31][C:3]1[C:2]([C:36]#[C:35][C:33]([OH:37])([CH3:34])[CH3:32])=[CH:30][C:6]2[C:7]3[N:8]([C:12]([C:18]4[N:22]([CH3:23])[N:21]=[C:20]([C:24]5[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=5)[N:19]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 86693129HCID 86693129, compound

Product 1

HCID 71715340HCID 71715340, compoundYield 35.3%

Procedure

The title compound was prepared similarly according to Procedure E. 10-bromo-9-fluoro-3-(1-methyl-3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 2-methyl-3-butyn-2-ol to afford 35.3% yield of the titled product. 1H NMR (400 MHz, DMSO) δ 8.73-8.67 (m, 3H), 7.99 (br s, 1H), 7.97-7.93 (m, 2H), 7.47 (br s, 1H), 7.06 (d, J=10.5 Hz, 1H), 5.53 (s, 1H), 4.58-4.52 (m, 2H), 4.38-4.28 (m, 2H), 3.83 (s, 3H), 1.51 (s, 6H). M+H=488.2

Workup

  1. customThe title compound was prepared similarly

Sources & evidence

ORD record
ord-d1e6436da3de4eb38c0017f4776ca5d0
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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