Hydrochloric Acid → HCID 22462197, compound

HRID 2306739Notes

Reaction equation

HRID 2306739 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]4[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:34][S:35]([NH:38][CH2:39][CH2:40][NH2:41])(=[O:37])=[O:36].Cl>O>[ClH:1].[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]4[O:31][C:30]([CH2:32][NH:41][CH2:40][CH2:39][NH:38][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:29][CH:28]=4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 533845N-(2-Aminoethyl)methanesulfonamideHCID 219523065-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-furan-2-carbaldehyde hydrochloride

Product 1

HCID 22462197HCID 22462197, compoundYield 156%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an analogous manner to Example 10, 5-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-furan-2-carbaldehyde hydrochloride (0.200 g, 0.436 mmol) was reacted with 2-(methanesulphonamido)ethylamine (0.350 g, 2.53 mmol). On completion of the reaction the mixture was acidified with dilute HCl and diluted with water, but no solid was formed. The mixture was concentrated in vacuo, and the residue was washed with acetone, 2N HCl and acetone again, and dried at 60° C. in vacuo to give the title compound as a yellow solid (0.210 g, 0.340 mmol, 78%); δH [2H6]DMSO 12.01 (1H, s), 9.82 (1H, br s), 9.77 (1H, s), 8.88 (1H, s), 8.40 (1H, d), 8.02 (1H, d), 7.76 (2H, d), 7.31-7.53 (6H, m), 7.14 (2H, d), 6.84 (1H, d), 5.18 (2H, s), 4.40 (2H, s), 3.34-3.48 (2H, m), 3.08-3.18 (2H, m), 2.96 (3H, s); m/z (M+1+) 544.

Workup

  1. customOn completion of the reaction the mixture
  2. customno solid was formed
  3. concentrationThe mixture was concentrated in vacuo
  4. washthe residue was washed with acetone, 2N HCl and acetone again
  5. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-84718c0596c2443a9c03a07a9eebd84b
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

Loading…