1-Ethynylcyclopentanol → 8-Fluoro-9-[2-(1-hydroxycyclopentyl)ethynyl]-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

HRID 575144Notes

Reaction equation

HRID 575144 reaction equation
Br[C:2]1[C:3]([F:19])=[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:20]([C:22]1([OH:27])[CH2:26][CH2:25][CH2:24][CH2:23]1)#[CH:21]>>[F:19][C:3]1[C:2]([C:21]#[C:20][C:22]2([OH:27])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:7][C:6]2[C:8]3[N:9]=[C:10]([C:16]([NH2:18])=[O:17])[S:11][C:12]=3[CH2:13][CH2:14][O:15][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 870741-EthynylcyclopentanolHCID 866930599-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

Product 1

HCID 717150478-Fluoro-9-[2-(1-hydroxycyclopentyl)ethynyl]-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

Procedure

9-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide (0.25 g) was reacted with 1-ethynylcyclopentanol similar to as described in Procedure E to afford 157 mg of 8-fluoro-9-[2-(1-hydroxycyclopentyl)ethynyl]-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide following reverse phase hplc purification. MS (Q1) 338 (M)+. 1H NMR (400 MHz, DMSO) δ 8.65 (d, J=8.6 Hz, 1H), 8.45 (s, 1H), 7.84 (s, 1H), 7.03 (t, J=25.1 Hz, 1H), 5.29 (d, J=38.1 Hz, 1H), 4.38 (t, J=4.8 Hz, 2H), 3.40 (t, J=4.8 Hz, 2H), 2.02-1.86 (m, 4H), 1.85-1.57 (m, 5H).

Sources & evidence

ORD record
ord-b482b0608ec14f88b2c0f56e72ee9ae5
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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