Hydrochloric Acid → HCID 68818490, compound

HRID 1816976Notes

Reaction equation

[CH:1]([C@:4]1([C:20]([N:22]2[CH2:31][CH2:30][C:29]3[N:28]=[CH:27][C:26]([C:32]([F:35])(F)[F:33])=[CH:25][C:24]=3[CH2:23]2)=[O:21])[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:11][CH2:10]2)[CH2:5]1)([CH3:3])[CH3:2].[OH-].[Li+].Cl.[CH3:39]O>>[F:35][C:32]([C:26]1[CH:27]=[N:28][C:29]2[CH2:30][CH2:31][N:22]([C:20]([C@@:4]3([CH:1]([CH3:2])[CH3:3])[CH2:8][CH2:7][CH:6]([N:9]4[CH2:10][CH2:11][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]4)[CH2:5]3)=[O:21])[CH2:23][C:24]=2[CH:25]=1)([F:33])[CH3:39]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 3939Lithium Hydroxide

HCID 57880550HCID 57880550, compound

Product 1

HCID 68818490HCID 68818490, compoundYield 91%

Procedure

To a solution of methyl [1-((3S)-3-isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)piperidin-4-yl]acetate (470 mgs, 0.92 mmol) in methanol (5 ml) was added 2N Lithium Hydroxide solution (1.8 ml, 3.7 mmol), the reaction was then stirred overnight at room temperature. The reaction was neutralized to pH=5 using 3N HCl. The crude was purified on reverse phase HPLC using 5%-100% ACN/H2O to yield [1-((3S)-3-{[3-(1,1-difluoroethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}-3-isopropylcyclopentyl)piperidin-4-yl]acetic acid (320 mgs, 91%), LC-MS 482 (M++1).

Workup

customThe crude was purified on reverse phase

Sources & evidence

ORD record: ord-e14fda7cdc92474b81b484929953d9f7
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598243B2

Reaction notes

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