3-{[(4-Fluorophenyl)sulfonyl]methyl}azetidine hydrochloride → 1-[(6-Chloro-1-benzothien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine

HRID 10222

Reaction equation

HRID 10222 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]2[CH2:16][NH:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl:17][C:18]1[CH:28]=[CH:27][C:21]2[C:22]([CH:25]=O)=[CH:23][S:24][C:20]=2[CH:19]=1>>[Cl:17][C:18]1[CH:28]=[CH:27][C:21]2[C:22]([CH2:25][N:15]3[CH2:16][CH:13]([CH2:12][S:9]([C:6]4[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=4)(=[O:11])=[O:10])[CH2:14]3)=[CH:23][S:24][C:20]=2[CH:19]=1

Participants

3

Reactant 2

HCID 219783933-{[(4-Fluorophenyl)sulfonyl]methyl}azetidine hydrochlorideHCID 823742046-Chloro-1-benzothiophene-3-carbaldehyde

Product 1

HCID 219783961-[(6-Chloro-1-benzothien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine

Procedure

Prepared according to the method of Example 23 using 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4) and 6-chloro-1-benzothiophene-3-carbaldehyde. 1H NMR (500 MHz, CDCl3) δ 7.92–7.88 (2H, m), 7.81 (1H, d, J=1.8 Hz), 7.72 (1H, d, J=8.5 Hz), 7.32 (1H, dd, J=1.9, 8.6 Hz), 7.26–7.22 (2H, m), 7.19 (1H, s), 3.73 (2H, s), 3.44 (2H, t, J=7.5 Hz), 3.37 (2H, d, J=7.3 Hz), 2.92 (2H, t, J=7.1 Hz), 2.87–2.80 (1H, m). m/z (ES+) 394 (M+H)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-609ecb2da5fb437e95b142568c998f9a
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Linked notes

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