Hydrochloric Acid → HCID 17885200, compound

HRID 1936812Notes

Reaction equation

HRID 1936812 reaction equation
Cl.[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.Cl.[NH2:35][CH2:36][CH2:37][S:38]([NH2:41])(=[O:40])=[O:39].Cl>C(N(CC)CC)C.O>[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:35][CH2:36][CH2:37][S:38]([NH2:41])(=[O:40])=[O:39])=[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 30215492-Aminoethanesulphonamide monohydrochlorideHCID 219523065-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-furan-2-carbaldehyde hydrochloride

Product 1

HCID 17885200HCID 17885200, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 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-aminoethylsulphonamide hydrochloride (0.200 g, 1.245 mmol) and triethylamine (10 drops). On completion of the reaction, the mixture was acidified with dilute HCl and diluted with water, to give the crude product as a precipitate collected by filtration. Treatment with triethylamine followed by purification by silica gel chromatography, eluting with 3-10% MeOH/CHCl3 gave the title compound as a yellow solid (0.085 g, 0.160 mmol, 37%); δH [2H6]DMSO 9.61 (2H, brs), 9.25 (1H,s), 8.58 (1H,s), 8.23 (1H,d), 7.77-7.88 (3H,m), 7.30-7.52 (5H,m), 7.26 (2H,s), 7.20 (1H,d), 7.08 (2H,d), 6.81 (1H,d), 5.14 (2H,s), 4.44 (2H,s), 3.34-3.60 (2H, m), 3.25-3.45 (2H, obscured by water); m/z (M+1+) 530.

Workup

  1. customOn completion of the reaction
  2. customto give the crude product as a precipitate
  3. filtrationcollected by filtration
  4. customTreatment with triethylamine followed by purification by silica gel chromatography
  5. washeluting with 3-10% MeOH/CHCl3

Sources & evidence

ORD record
ord-4830bc97dcb24aad84bb236b8771a28d
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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