Hydrochloric Acid → HCID 17885200, compound

HRID 2306740Notes

Reaction equation

HRID 2306740 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-3e700ee264e84035b14c26c50f21a3fe
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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