Cyclopropanecarbonyl chloride → HCID 10205776, compound

HRID 411292Notes

Reaction equation

HRID 411292 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].C(=O)(O)[O-].[Na+].[CH:36]1([C:39](Cl)=[O:40])[CH2:38][CH2:37]1>C(OCC)(=O)C>[NH2:30][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([N:15]([CH2:17][C:18]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:20][N:21]([C:39]([CH:36]3[CH2:38][CH2:37]3)=[O:40])[CH2:22][CH2:23]2)[CH3:16])[N:7]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 11486612HCID 11486612, compound

Product 1

HCID 10205776HCID 10205776, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (125 mg), ethyl acetate (10 ml) and aq. sodium bicarbonate (10 ml) was stirred vigorously while 40 μL of cyclopropylcarbonyl chloride were added slowly via syringe. After 30 min., the reaction mixture was worked up as usual to yield 1-(4-{[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-methyl}-4-phenyl-piperidin-1-yl)-1-cyclopropyl-methanone 12, MS: 476 ([M+H]+) The crude base was converted to the hydrochloride salt as a white powder (120 mg).

Workup

  1. additionwere added slowly via syringe

Sources & evidence

ORD record
ord-f6bfec29783245b4a7071489919acea7
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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