Benzoyl chloride, 3,4-dichloro- → HCID 67004347, compound

HRID 564390Notes

Reaction equation

HRID 564390 reaction equation
ClC1C=C(C=CC=1Cl)C([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.ClC1C=C(C=CC=1Cl)C(Cl)=[O:40]>>[NH2:7][CH2:8][C:9]([NH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:18][CH2:19][O:40][CH2:21][CH2:22]2)[CH2:13]1)=[O:10].[NH2:7][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:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[CH2:19][CH2:18]2)[CH2:13]1)=[O:10]

Participants

4

Reactant 2

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

Product 2

HCID 67004347HCID 67004347, compoundHCID 67004917HCID 67004917, 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-(trifluoromethoxy)benzoyl chloride for 3,4-dichlorobenzoylchloride, as well as 2-amino-N-[(3R)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]acetamide for 2-amino-N-{(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}acetamide, and was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.40-1.78 (m, 5H), 2.12-2.36 (m, 3H), 2.62 (d, J=5.4 Hz, 2H), 2.83 (m, 1H), 2.94 (m, 1H), 3.33 (m, 2H), 3.91 (m, 2H), 4.06 (d, J=5.4 Hz, 2H), 4.39 (m, 1H), 7.16 (d, J=7.8 Hz, 1H), 7.30 (m, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.70 (m, 1H). MS m/z: 416 (M+1).

Sources & evidence

ORD record
ord-6f8a08d9e1914ca180d9c4f1c4f66f5d
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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