4-Hydroxypyrrolidine → 5-(3-Hydroxy-pyrrolidin-1-yl)-1-methyl-1h-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12841

Reaction equation

HRID 12841 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([CH3:20])[C:18]=1Cl)=[O:13])[CH2:8]2.[CH2:21]1[CH:25]([OH:26])[CH2:24][NH:23][CH2:22]1>>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([CH3:20])[C:18]=1[N:23]1[CH2:22][CH2:21][CH:25]([OH:26])[CH2:24]1)=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250140395-(3-Hydroxy-pyrrolidin-1-yl)-1-methyl-1h-pyrazole-4-carboxylic acid adamantan-2-ylamide

Procedure

Heating a mixture of 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 5, 88 mg; 0.30 mmol) and DL-3-pyrrolidinol (0.25 mL; 3.0 mmol) under microwave irradiation according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-(3-hydroxy-pyrrolidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (68 mg, 66%) as an off-white powder. ES-HRMS m/e calcd for C19H29N4O2 (M+H+) 345.2285, found 345.2281.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-(3-hydroxy-pyrrolidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (68 mg, 66%) as an off-white powder

Sources & evidence

ORD record
ord-72d140f22a01450bba8fbc9a3a48a46d
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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