Ammonia → HCID 58032153, compound

HRID 2167282Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=O)=[CH:11][CH:12]=2)[C@H:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:28][N:27]=[N:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:6][C@@H:5]1[CH3:29])(=[O:3])[CH3:2].[NH3:30]>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH2:30])=[O:16])=[CH:11][CH:12]=2)[CH:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:28][N:27]=[N:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:6][CH:5]1[CH3:29])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 222Ammonia

HCID 66625441HCID 66625441, compound

Product 1

HCID 58032153HCID 58032153, compound

Procedure

Reactions and treatments were carried out in the same manner as in Example 118, using 61.2 mg of (2S,4R)-1-acetyl-2-methyl-4-{[4-(1,2,3-thiadiazol-5-yl)phen yl]amino}-1,2,3,4-tetrahydroquinoline-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, 44.9 mg (73.5%, cis:trans=20:1) of the title compound was obtained as a pale yellow amorphous substance.

Sources & evidence

ORD record: ord-ef8f36acd95a413abaf29b6ad279ac8d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045423B2

Reaction notes

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