Ammonia → HCID 66624749, compound

HRID 2167269Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14](O)=[O:15])=[CH:11][CH:12]=2)[C@H:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2].[NH3:26]>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH2:26])=[O:15])=[CH:11][CH:12]=2)[C@H:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 222Ammonia

HCID 66626039HCID 66626039, compound

Product 1

HCID 66624749HCID 66624749, compound

Procedure

Reactions and treatments were carried out in the same manner as in Example 118, using 41.1 mg of (2S,4R)-1-acetyl-4-(4-chlorophenoxy)-2-methyl-1,2,3,4-tetra hydroquinoline-6-carboxylic acid instead of (2S,4R)-1-acetyl-2-methyl-4-(4-morpholinophenoxy)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, and using aqueous ammonia instead of monomethylamine. Thus, 58.5 mg (95.6%, cis-form only) of the title compound was obtained as a white crystalline powder.

Sources & evidence

ORD record: ord-cdcd7acc959841c2a6f70bb3e64d84a5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045423B2

Reaction notes

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