2,3-Dihydro-1-benzofuran-5-carbonyl chloride → HCID 57841334, compound

HRID 733550Notes

Reaction equation

Cl.[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][NH:19][C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[O:35]1[C:39]2[CH:40]=[CH:41][C:42]([C:44](Cl)=[O:45])=[CH:43][C:38]=2[CH2:37][CH2:36]1>>[CH2:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][N:19]([C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)[C:44]([C:42]3[CH:41]=[CH:40][C:39]4[O:35][CH2:36][CH2:37][C:38]=4[CH:43]=3)=[O:45])=[CH:16][CH:15]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:4][CH3:5]

Participants

Reactant 2

HCID 27761532,3-Dihydro-1-benzofuran-5-carbonyl chloride

HCID 684196986-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride

Product 1

HCID 57841334HCID 57841334, compound

Procedure

The titled compound was prepared following the procedure J using 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride and 2,3-dihydro-1-benzofuran-5-carbonyl chloride as a colorless oil (92%). 1H NMR (CDCl3, 300 MHz) δ 7.66 (d, J=2.7 Hz, 1H), 7.44 (m, 4H), 7.34 (brs, 1H), 7.26 (d, J=8.3 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H), 7.02 (m, 1H), 6.97 (dd, J=8.6, 2.7 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 6.52 (d, J=8.3 Hz, 1H), 5.12 (s, 2H), 4.55 (t, J=8.9 Hz, 2H), 3.12 (t, J=8.9 Hz, 2H), 2.62 (t, J=7.8 Hz, 2H), 1.69 (s, 6H), 1.61 (m, 2H), 1.36 (m, 2H), 0.93 (t, J=7.4 Hz, 3H). M+ (ESI): 586.4. HPLC, Rt: 6.05 min (Purity: 100%).

Sources & evidence

ORD record: ord-b398142db2d344bd85f97457d8e56b14
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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