1,4-Butanediol → HCID 44595461, compound

HRID 1916992Notes

Reaction equation

HRID 1916992 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:10]([OH:18])([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[C:4]2=[CH:3][CH:2]=1)=[O:8].[CH2:28](O)[CH2:29][CH2:30][CH2:31][OH:32]>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2([O:18][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:8])[N:9]2[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 80641,4-ButanediolHCID 51349701HCID 51349701, compound

Product 1

HCID 44595461HCID 44595461, compoundYield 67%

Procedure

The named compound was synthesised from 2-(4-(aminomethyl)benzonitrile)-3-(4-chlorophenyl)-3-hydroxyisoindolin-1-one (513 mg, 1.37 mmol, 1 equiv.) and 1,4-butanediol (616 mg, 6.85 mmol, 5 equiv.) using General Procedure B and obtained as a white solid (302 mg, 67%). 1H NMR (300 MHz, CDCl3): 7.94-7.91 (m, 1H, C(O)═C═CH), 7.55-7.52 (m, 2H, Ar—H), 7.47 and 7.33 (d: A2B2, J=8.4 Hz, 4H, Ar—H), 7.20 (m, 4H, Ar—H), 7.13-7.10 (m, 1H, Ar—H), 4.60 and 4.24 (d: AB, J=15.0 Hz, 2H, NCH2), 3.56 (t, J=5.4 Hz, 2H, HOCH2), 2.80-2.74 (m, 2H, OCH2), 1.53-1.16 (m, 4H, CH2). 13C NMR (75 MHz, CDCl3): 168.18, 145.32, 142.86, 137.20, 134.77, 132.90, 131.86, 131.46, 129.99, 129.85, 128.61, 127.95, 123.77, 123.08, 118.41, 111.33, 94.78, 62.82, 62.34, 42.68, 29.41, 25.67. Anal.: calc. for C29H23ClN2O3+0.2 H2O: C, 69.37; H, 5.16; N, 6.22. Found: C, 69.29; H, 5.20, N: 6.04.

Sources & evidence

ORD record
ord-8076a59b457944b29eaa9a8b061e5491
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

Loading…