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

HRID 484448Notes

Reaction equation

HRID 484448 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][CH2:25][NH2:26])=[CH:20][CH:19]=2)=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:28])=[CH:10][C:11]=2[Cl:27])[NH:6]1)([OH:4])=[O:3].Cl.[C:30]([C@H]1C[C@H](NC(C2C=CC=C(CN)C=2)=O)C2C(=CC(Cl)=CC=2Cl)N1)(O)=O>>[ClH:27].[CH3:30][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][CH2:25][NH2:26])=[CH:20][CH:19]=2)=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:28])=[CH:10][C:11]=2[Cl:27])[NH:6]1)=[O:4]

Participants

3

Reactant 2

HCID 67690807Trans-2-carboxy-5,7-dichloro-4-(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochlorideHCID 67690934trans-2-Carboxy-5,7-dichloro-4-(4-aminoethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

Product 1

HCID 67691337Trans-2-methoxycarbonyl-5,7-dichloro-4-(4-aminoethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

Procedure

This compound was prepared by the method given for Example 82 using trans-2-carboxy-5,7-dichloro-4-(4-aminoethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride Example 85, in the 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. 218° C. (dec). δ (DMSO, 360 MHz) 1.78 (1H, ddd, J=13.2, 12.8 and 4.1 Hz, CHACHBHCCHD), 2.25 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 2.92 (2H, t, J=7.0 Hz, CHE2CHF2), 3.04 (2H, t, J=7.0 Hz, CHE2CHF2), 3.71 (3H, s, CH3), 4.06 (1H, dd, J=12.5 and 2.4 Hz, CHACHBHCCHD), 5.26 (1H, m, CHACHBHCCHD), 6.69 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.91 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.94 (1H, s, Ar NHCH), 7.33 (2H, d, J=8.1 Hz, Ar-H), 7.86 (2H, d, J=8.1 Hz, Ar-H), 7.96 (2H, br, s, NH2), 8.70 (1H, d, J=7.1 Hz, NHCO); m/e (CI+, NH3) 422 (M+1); Found C, 48.59; H, 4.55; N, 8.48.C20H21Cl2N3O3.2HCl requires C, 48.51; H, 4.68; N, 8.48%.

Workup

  1. customThis compound was prepared by the method

Sources & evidence

ORD record
ord-4c6b00333e384a8db8b1d79aa33595e6
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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