Benzoyl chloride, 3,4-dichloro- → HCID 57813990, compound

HRID 564389Notes

Reaction equation

HRID 564389 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1Cl)[C:5]([NH:7][CH2:8][C:9]([NH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)[CH2:13]1)=[O:10])=[O:6].ClC1C=C(C=CC=1Cl)C(Cl)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[C:5]([NH:7][CH2:8][C:9]([NH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[CH2:21][CH2:22]2)[CH2:13]1)=[O:10])=[O:6]

Participants

3

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 57814014HCID 57814014, compound

Product 1

HCID 57813990HCID 57813990, compound

Procedure

The title compound was synthesized in similar fashion to 3,4-Dichloro-N-[2-({(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]benzamide, substituting 3-chlorobenzoylchloride for 3,4-dichlorobenzoylchloride, and was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.63-1.64 (m, 3H), 1.86-1.90 (m, 2H), 2.01-2.44 (m, 3H), 2.56-2.74 (m, 4H), 2.92-3.00 (m, 1H), 3.43 (d, J=11.1 Hz, 2H), 3.70 (s, 3H), 4.04 (d, J=4.2 Hz, 2H), 4.43 (b, 1H), 6.55 (d, J=6.0 Hz, 1H), 6.74-6.85 (m, 4H), 7.06 (b, 1H), 7.30 (t, J=8.5 Hz, 1H), 7.42 (d, J=7.5 Hz, 2H), 7.63 (d, J=8.1 Hz, 1H), 7.27 (s, 1H). MS m/z: 471 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-18ef4a3f04844303ba3957992d37c298
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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