2-Methyl-3-butyn-2-ol → HCID 71714695, compound

HRID 575180Notes

Reaction equation

HRID 575180 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:15][CH2:14][CH2:13][C:12]3[S:11][C:10]([C:16]([NH2:18])=[O:17])=[N:9][C:8]=3[C:6]=2[CH:7]=1.[CH3:19][C:20]([CH3:24])([C:22]#[CH:23])[OH:21]>>[OH:21][C:20]([CH3:24])([CH3:19])[C:22]#[C:23][C:2]1[CH:3]=[CH:4][C:5]2[O:15][CH2:14][CH2:13][C:12]3[S:11][C:10]([C:16]([NH2:18])=[O:17])=[N:9][C:8]=3[C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 582039029-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

Product 1

HCID 71714695HCID 71714695, compound

Procedure

9-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide (0.15 g) was reacted with dimethyl ethynyl carbinol similar to as described in Procedure E to afford 56.9 mg of 9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide following reverse phase hplc purification. MS (Q1) 329 (M)+. 1H NMR (400 MHz, DMSO) δ 8.57 (d, J=2.1 Hz, 1H), 8.39 (s, 1H), 7.84 (s, 1H), 7.27 (dd, J=8.3, 2.1 Hz, 1H), 7.01 (d, J=8.3 Hz, 1H), 5.40 (s, 1H), 4.34 (t, J=4.9 Hz, 2H), 3.41 (t, J=4.9 Hz, 2H), 1.49 (s, 6H).

Sources & evidence

ORD record
ord-237011470d244dfe9cd7fbdcb8353498
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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