Dimethylamine, hydrochloride → 5-cyclopropyl-N-[1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480276Notes

Reaction equation

[CH:1]1([C:4]2[C:5]([O:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]([OH:16])=O)=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[CH3:29][NH:30][CH3:31]>>[CH:1]1([C:4]2[C:5]([O:21][C@@H:22]([CH3:27])[C:23]([F:25])([F:26])[F:24])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:17]([CH3:19])([CH3:20])[CH3:18])[C:14]([N:30]([CH3:31])[CH3:29])=[O:16])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 10473Dimethylamine, hydrochloride

HCID 902035392-[[5-cyclopropyl-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoic acid

Product 1

HCID 902042405-cyclopropyl-N-[1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 2-[[5-cyclopropyl-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoic acid (Example 199b) and dimethylamine hydrochloride as starting materials and isolated (31 mg, 57%); MS (ESI, m/z): 416.6 (M+H+).

Workup

customisolated (31 mg, 57%)

Sources & evidence

ORD record: ord-fce482ad968d4063bcd9d89e65ba8d23
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

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