1-Ethynylcyclopentanol → HCID 71714709, compound

HRID 575179Notes

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.[C:19]([C:21]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]1)#[CH:20]>>[OH:26][C:21]1([C:19]#[C:20][C:2]2[CH:3]=[CH:4][C:5]3[O:15][CH2:14][CH2:13][C:12]4[S:11][C:10]([C:16]([NH2:18])=[O:17])=[N:9][C:8]=4[C:6]=3[CH:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Reactant 2

HCID 870741-Ethynylcyclopentanol

HCID 582039029-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

Product 1

HCID 71714709HCID 71714709, compound

Procedure

9-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide (0.15 g) was reacted with 1-ethynylcyclopentanol similar to as described in Procedure E to afford 46.2 mg of 9-[2-(1-hydroxycyclopentyl)ethynyl]-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide following reverse phase hplc purification. MS (Q1) 355 (M)+. 1H NMR (400 MHz, DMSO) δ 8.58 (d, J=2.1 Hz, 1H), 8.40 (s, 1H), 7.84 (s, 1H), 7.27 (dd, J=8.3, 2.1 Hz, 1H), 7.01 (t, J=7.6 Hz, 1H), 5.26 (s, 1H), 4.34 (t, J=4.9 Hz, 2H), 3.41 (t, J=4.9 Hz, 2H), 2.00-1.82 (m, 4H), 1.82-1.59 (m, 5H).

Sources & evidence

ORD record: ord-8e417a83aa834b78b7fa2b281a8e817c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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