3,4-Dichlorobenzoic acid → HCID 18353766, compound

HRID 430065Notes

Reaction equation

HRID 430065 reaction equation
O[N:2]1[C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.Cl.C[N:13](C)[CH2:14][CH2:15][CH2:16]N=C=NCC.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:27]([OH:29])=[O:28].C([N:37]([CH:40]([CH3:42])[CH3:41])[CH2:38][CH3:39])(C)C.CN([CH:46]=[O:47])C>ClCCl>[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:27]([NH:2][CH2:6][CH2:5][CH2:10][CH2:9][CH2:8][NH:7][C:38]1[NH:37][C:40]2[C:41]([C:46](=[O:47])[CH:39]=1)=[CH:16][CH:15]=[CH:14][CH:42]=2)=[O:29].[CH3:27][OH:28].[NH3:13]

Participants

8

Reactant 5

HCID 58173,4-Dichlorobenzoic acidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 2

HCID 18353766HCID 18353766, compoundHCID 21705897Ammonia methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by an analogous procedure to that described in example 24 from compound 30b (0.07 g, 0.22 mmol), 1-hydroxy-7-azabenzotriazole (0.03 g, 0.22 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.05 g, 0.26 mmol), 3,4-dichlorobenzoic acid (0.042 g, 0.22 mmol) and diisopropylethylamine (0.115 ml, 0.66 mmol) in dry DMF (2 ml). Chromatography over silica gel eluting with increasing amounts of 9:1 methanol/ammonia in dichloromethane gave a white solid (35%). δH (CD3OD) 1.5-1.9 (6H, envelop), 3.3-3.5 (4H, m), 5.70 (1H, s), 7.30 (1H, t), 7.45 (1H, d), 7.58 (1H, d), 7.65 (1H, d), 7.77 (1H, dd), 8.02 (1H, d), 8.11 (1H, d). MS (ES+) 420 (71%), 418 (100%) MH+.

Sources & evidence

ORD record
ord-a0c366daed4a44308ada33acb5bfa4c9
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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