HCID 118898597, compound → HCID 117653049, compound

HRID 588385Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[CH:7][C:6]=1[C:11]1[CH:39]=[CH:38][C:14]([C:15]([N:17]([C:31]2[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][N:32]=2)[C@@H:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2)=[O:16])=[CH:13][CH:12]=1)=[O:4]>CO.[OH-].[K+]>[C:27]([O:26][C:24]([N:20]1[CH2:21][CH2:22][CH2:23][C@@H:18]([N:17]([C:31]2[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][N:32]=2)[C:15]([C:14]2[CH:38]=[CH:39][C:11]([C:6]3[CH:7]=[N:8][N:9]([CH3:10])[C:5]=3[C:3]([OH:4])=[O:2])=[CH:12][CH:13]=2)=[O:16])[CH2:19]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of the product of Step 1 of EXAMPLE 13, tert-butyl (3R)-3-[{4-[5-(methoxycarbonyl)-1-methyl-1H-pyrazol-4-yl]benzoyl}(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate (0.85 g, 0.59 mmol) in MeOH (2 mL) and potassium hydroxide solution in MeOH (1.67 mL, 1M solution, 1.67 mmol) was heated to 70° C. in a sealed pressure tube for 2 h. The reaction mixture was then concentrated and toluene (10 mL) was added to the mixture. The solvents were evaporated in vacuo and dried under vacuum for 2 h. The solid was then slurried in methyl tert-butyl ether (15 mL) and heptanes (15 mL) for 1 h, collected via filtration and dried under vacuum for 16 h to afford 4-(4-{[(3R)-1-(tert-butoxycarbonyl)piperidin-3-yl](3-methylpyridin-2-yl)carbamoyl}phenyl)-1-methyl-1H-pyrazole-5-carboxylic acid (800 mg, 90%).

Workup

concentrationThe reaction mixture was then concentrated
additiontoluene (10 mL) was added to the mixture
customThe solvents were evaporated in vacuo
customdried under vacuum for 2 h
filtrationcollected via filtration
customdried under vacuum for 16 h

Sources & evidence

ORD record: ord-1320548ad2ae4ac19443db65aa9141b8
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227956B2

Reaction notes

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