Diisopropylethylamine → 1-Acetyl-6-(3-[adamantan-1-yl]propionyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

HRID 557564Notes

Reaction equation

HRID 557564 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2].[C:24]12([CH2:34][CH2:35][C:36](O)=[O:37])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2.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:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:36](=[O:37])[CH2:35][CH2:34][C:24]34[CH2:33][CH:28]5[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]5)[CH2:25]3)[CH2:31]4)=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7134943-(1-Adamantyl)propanoic acidHCID 28370841-(6-amino-2,2,4-trimethyl-4-phenyl-3,4-dihydroquinolin-1(2H)-yl)ethanoneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 179629051-Acetyl-6-(3-[adamantan-1-yl]propionyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Condensation of 1-acetyl-6-amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (10 mg) with 3-(adamantan-1-yl)propionic acid (10 mg) under the agency of HATU (25 mg) and N,N-diisopropylethylamine (22 μl) in dichloromethane (1 ml) was performed according to the method described in example 11.

Sources & evidence

ORD record
ord-a93546a468fb4933945a5029ba49a268
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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