Piperazine → HCID 3863656, compound

HRID 388413Notes

Reaction equation

HRID 388413 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13](C3N=C(N)C4C(=CC(OC)=C(OC)C=4)N=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.N1CCNCC1.ClC1SC(S(Cl)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 11340368HCID 11340368, compound

Product 1

HCID 3863656HCID 3863656, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Method B (14, 20, 23, 32). 2-[4-(5-Chloro-thiophene-2-sulfonyl)-piperazin-1-yl]-6,7-dimethoxy-quinazolin-4-ylamine (14): To a solution of piperazine (0.517 g, 6.0 mmol) and 5-chloro-thiophene-2-sulfonyl chloride (0.436 g, 2.0 mmol) in methanol (10 mL), the mixture was stirred at room temperature for 1 h. The solvent was evaporated, and the residue was purified with silica gel chromatography to obtain 1-(5-chloro-thiophene-2-sulfonyl)-piperazine. The intermediate (0.266 g, 1.0 mmol) and 4-amino-2-chloro-6,7-dimethoxy-quinazoline (0.251 g, 1.0 mmol) in 1-butanol (5 mL) were stirred under reflux overnight, and cooled to 80° C. The collected solid product was washed with ethyl acetate (2×10 mL), stirred in methanol (30 mL) under reflux for 1 h, filtered, washed with methanol (2×10 ml) to yield compound 14. 1HNMR (DMSO-d6) δ 3.06-3.08 (m, 4H), 3.80 (s, 3H), 3.84 (s, 3H), 3.94 (s, 4H), 7.36 (s, 1H), 7.37 (s, 1H), 7.59 (s, 1H), 7.60 (s, 1H). HRMS (M+H)+ calcd for C18H21ClN5O4S2 470.0718, found 470.0740. Anal. (C18H20ClN5O4S2.HCl) C, H, N.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-fb8e7b1e51074bee962eedd967bb4c36
Source dataset
uspto-grants-2013_02
Patent number
US08377948B2

Reaction notes

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