Hydrochloric Acid → HCID 22462197, compound

HRID 1936811Notes

Reaction equation

HRID 1936811 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-92231a1d0edf4f16950bb07080ee1615
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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