Triethylamine → HCID 10301355, compound

HRID 411297Notes

Reaction equation

HRID 411297 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]([CH2:17][C:18]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:16])[N:7]=[C:6]2[NH2:30].[CH3:31][N:32]([CH3:37])[S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>O1CCCC1.O>[CH3:31][N:32]([CH3:37])[S:33]([N:21]1[CH2:20][CH2:19][C:18]([CH2:17][N:15]([C:8]2[N:7]=[C:6]([NH2:30])[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=2)[CH3:16])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22]1)(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 11486612HCID 11486612, compound

Product 1

HCID 10301355HCID 10301355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (350 mg), dimethylsulfamoyl chloride (140 μl), and triethylamine (240 μl) in tetrahydrofuran (10 ml) was stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with ethyl acetate. The product was chromatographed on silica gel to yield 4-{[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-methyl}-4-phenyl-piperidine-1-sulfonic acid dimethylamide 19, MS: 515 ([M+H]+).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-b43ff2e13afb4d75b7bbcbf8852fb4a3
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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