HCID 67691387, compound → HCID 67856768, compound

HRID 484440Notes

Reaction equation

HRID 484440 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:14][C@H:13]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=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]>CS(C)=O>[C:3]([C@H:5]1[CH2:14][C@H:13]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=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:2]

Participants

3

Reactant 1

HCID 67691387HCID 67691387, compound

Product 1

HCID 67856768HCID 67856768, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared by the method given for Example 38 step b using trans-2-methoxycarbonyl-5,7-dichloro-4(4-iodophenylaminocarbonyl)amino-1,2,3,4-tetrahydroquinoline in place of trans-2-methoxycarbonyl-5,7-dichloro-4(phenylaminocarbonyl)amino-1,2,3,4-tetrahydroquinoline to give the title compound as colourless crystals, m.p. 224°-226° C. δ (DMSO, 360 MHz) 1.62 (1H, ddd, J=13.1, 12.9 and 3.4 Hz, CHACHBHCCHD), 2.31 (1H, dm, J=13.1 Hz, CHACHBHCCHD), 3.87 (1H, dd, J=12.7 and 2.7 Hz, CHACHBHCCHD), 4.92 (1H, m, CHACHBHCCHD), 6.58 (1H, d, J=6.6 Hz, NHCONHAr), 6.68 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.79 (1H, s, ArNHCH), 6.88 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.25 (2H, d, J=8.7 Hz-Ar-H), 7.54 (2H, d, 8.7 Hz, Ar-H), 8.26 (1H, s, NHCONHAr); m/e (FAB+) 506 (M+1) 93 (100%); Found C, 40.14; H, 2.80; N, 8.20; C17H14Cl2N3IO3.O.1H2O requires C, 40.20; H, 2.82; N, 8.24%.

Workup

  1. customThis compound was prepared by the method

Sources & evidence

ORD record
ord-b4eb22efd5ac49548a82a8326012cd64
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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