Sodium Carbonate → HCID 10301907, compound

HRID 411294Notes

Reaction equation

HRID 411294 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].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]=[C:38]=[O:39])[CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C1(C)C=CC=CC=1>[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38]([N:21]2[CH2:20][CH2:19][C:18]([CH2:17][N:15]([C:8]3[N:7]=[C:6]([NH2:30])[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=3)[CH3:16])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22]2)=[O:39])[CH:32]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27604933-IsocyanatopyridineHCID 11486612HCID 11486612, compound

Product 1

HCID 10301907HCID 10301907, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (340 mg) in dichloromethane (5 mL) was slowly added dropwise with stirring a dilute solution of 3-pyridylisocyanate in toluene. The progress of the reaction was monitored by TLC. After completion of the reaction, aq. sodium carbonate was added and the mixture was extracted with dichloromethane. The extract was washed with water, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel to yield 4-{[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-methyl}-4-phenyl-piperidine-1-carboxylic acid pyridin-3-ylamide 15, MS: 528 ([M+H]+). Treatment of the product with HCl in methanol/ethyl acetate gave 242 mg of the hydrochloride salt.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-29169686d8d74b609d5e09fbb79459fe
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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