Ammonia → HCID 178514685, compound

HRID 2247154Notes

Reaction equation

HRID 2247154 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].NC1C=C(C=CC=1N)C(N)=O.[Cl:24][C:25]1[CH:40]=[CH:39][C:28]([C:29]([C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1.C1(C2(C3C=CC(C=O)=CC=3)OCCO2)C=CC=CC=1.N>CO>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([C:31]2[CH:38]=[CH:37][C:34]([C:35]3[NH:8][C:7]4[CH:6]=[CH:5][C:4]([S:9]([NH2:12])(=[O:10])=[O:11])=[CH:3][C:2]=4[N:1]=3)=[CH:33][CH:32]=2)=[O:30])=[CH:39][CH:40]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 27359273,4-diaminobenzenesulfonamideHCID 10706104HCID 10706104, compoundHCID 12925059HCID 12925059, compoundHCID 212178433,4-Diaminobenzamide

Product 1

HCID 178514685HCID 178514685, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared as described in Example 1 substituting 3,4-diamino-benzenesulfonamide for 3,4-diamino-benzamide and 4-(4-chloro-benzoyl)-benzaldehyde for 4-(2-phenyl-[1,3]dioxolan-2-yl)-benzaldehyde in Step C (reaction mixture was heated to 60° C.). TLC (silica, 1% methanol saturated with ammonia/9% methanol/CH2Cl2): Rf=0.32. HPLC (Method A): Rt=8.03. MS (ESI+): mass calculated for C20H14ClN3O3S, 411.0; m/z found, 412.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6): δ 13.48 (br s, 1H), 8.31 (d, J=8.3 Hz, 2H), 8.16 (br s, 1H), 7.88 (d, J=8.3 Hz, 2H), 7.76 (br s, 1H), 7.74 (d, J=8.5 Hz, 2H), 7.73 (br s, 1H), 7.60 (d, J=8.5 Hz, 2H), 7.25 (br s, 2H).

Sources & evidence

ORD record
ord-85e758c5f54a4058a6e370adf52f4321
Source dataset
uspto-grants-2010_03
Patent number
US07687639B2

Reaction notes

Loading…