Sodium Hydroxide → HCID 10144138, compound

HRID 411295Notes

Reaction equation

HRID 411295 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].[O:31]1[C:36]2[CH:37]=[CH:38][C:39]([CH:41]=O)=[CH:40][C:35]=2[O:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.ClCCl>[O:31]1[C:36]2[CH:37]=[CH:38][C:39]([CH2:41][N:21]3[CH2:20][CH2:19][C:18]([CH2:17][N:15]([CH3:16])[C:8]4[N:7]=[C:6]([NH2:30])[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=4)([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:23][CH2:22]3)=[CH:40][C:35]=2[O:34][CH2:33][CH2:32]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11486612HCID 11486612, compound

Product 1

HCID 10144138HCID 10144138, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (250 mg) and 1,4-benzodioxan-6-carboxaldehyde (105 mg) in 1,2-dichloroethane (5 ml) was added sodium triacetoxyborohydride (140 mg) in one portion. The mixture was stirred at room temperature for two days. Aqueous NaOH (1N, 5 ml) was added and stirring was continued for one hour. The product was isolated by extraction with dichloromethane and purified by flash chromatograpy, to yield N2-[1-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-phenyl-piperidin-4-ylmethyl]-6,7-dimethoxy-N2-methyl-quinazoline-2,4-diamine 16, MS: 556 ([M+H]+). Treatment of the product with HCl in methanol/ethyl acetate gave 320 mg of the dihydrochloride salt.

Workup

  1. stirringstirring
  2. waitwas continued for one hour
  3. custompurified by flash chromatograpy

Sources & evidence

ORD record
ord-f8c9fae0fc7448b185e199e97a163b6b
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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