4-Methoxybenzyl alcohol → 1-Acetyl-6-(4-methoxybenzyloxy)carbonyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

HRID 557576Notes

Reaction equation

HRID 557576 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[C:11]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([C:24](O)=[O:25])=[CH:21][CH:22]=2)[C:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([CH3:27])[CH2:16][C:15]1([CH3:35])[CH3:34])(=[O:13])[CH3:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>ClCCl>[C:11]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([O:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:25])=[CH:21][CH:22]=2)[C:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([CH3:27])[CH2:16][C:15]1([CH3:35])[CH3:34])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 179628841-Acetyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline-6-carboxylic acid

Product 1

HCID 179629071-Acetyl-6-(4-methoxybenzyloxy)carbonyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Condensation of 4-methoxybenzylalcohol (6.2 mg) with 1-acetyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline-6-carboxylic acid (10 mg), under the agency of HATU (23 mg) and N,N-diisopropylethylamine (19 μl) in dichloromethane (2 ml) was performed according to the method described in example 11.

Sources & evidence

ORD record
ord-26eb0cd6baa84400914646f3a02e2f90
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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