4-Methoxybenzylamine → HCID 69022148, compound

HRID 1007306Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[C:18](Cl)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[C:18]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

Under argon atmosphere, a solution of 1.75 g of (1R,2S)-N-tert-butoxycarbonyl-2-(2-chloro-6-methoxyquinazolin-4-yl)aminocyclohexylamine and 1.47 g of 4-methoxybenzylamine in 100 mL of anhydrous toluene was combined with 97 mg of palladium acetate, 268 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 1.03 g of sodium tert-butoxide, and stirred at 70° C. for 5 hours. The reaction solvent was concentrated, and then combined with water, extracted with chloroform, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain 1.62 g of the desirable compound.

Workup

concentrationThe reaction solvent was concentrated
extractionextracted with chloroform
customdried
distillationAfter the solvent was distilled off
customthe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-26c468b1926542d7954fb90efc715632
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794389B2

Reaction notes

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