trans-2-Carboxy-5,7-dichloro-4(4-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride → Trans-2-methoxycarbonyl-5,7-dichloro-4-(4-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

HRID 484447Notes

Reaction equation

HRID 484447 reaction equation
Cl.[C:2]([C@H:5]1[CH2:14][C@H:13]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=2)=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:27])=[CH:10][C:11]=2[Cl:26])[NH:6]1)([OH:4])=[O:3].Cl.[C:29]([C@H]1C[C@H](NC(C2C=CC=C(CN)C=2)=O)C2C(=CC(Cl)=CC=2Cl)N1)(O)=O>CS(C)=O>[ClH:26].[CH3:29][O:3][C:2]([C@H:5]1[CH2:14][C@H:13]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=2)=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:27])=[CH:10][C:11]=2[Cl:26])[NH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 67690562trans-2-Carboxy-5,7-dichloro-4(4-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochlorideHCID 67690807Trans-2-carboxy-5,7-dichloro-4-(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

Product 1

HCID 67691609Trans-2-methoxycarbonyl-5,7-dichloro-4-(4-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared by the method given for Example 82 using trans-2-carboxy-5,7-dichloro-4(4-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride, Example 83, in place of trans-2-carboxy-5,7-dichloro-4(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride to give the title compound as a colourless crystalline solid m.p. 238°-240° C. δ (DMSO, 360 MHz), 1.80 (1H, ddd, J=13.0, 12.5 and 4.1 Hz, CHACHBHCCHD), 2.26 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 3.71 (3H, s, CH3), 4.07 (3H, m, CHACHBHCCHD and CH2NH2), 5.26 (1H, m, CHACHBHCCHD), 6.68 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.91 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.95 (1H, s, NH), 7.53 (2H, d, J=8.2 Hz, Ar-H), 7.91 (2H, d, J=8.2 Hz, Ar-H), 8.38 (2H, br s, NH2), 8.73 (1H, d, J=7.2 Hz, NHCO); m/e (CI+ , NH3), 408 (M+1), 15 (100%; Found C, 48.87; H, 4.37; N, 8.95; C19H19Cl2N3O3.1.6 HCl requires C, 48.91; H, 4.45; N, 9.10%.

Workup

  1. customThis compound was prepared by the method

Sources & evidence

ORD record
ord-f8dfb981fb7a4cbc8b19bf03bb625f34
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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