Thiomorpholine → Methyl-5-thiomorpholin-4-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12862

Reaction equation

HRID 12862 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.[NH:21]1[CH2:26][CH2:25][S:24][CH2:23][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:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1)=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 67164ThiomorpholineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 58972884Methyl-5-thiomorpholin-4-yl-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, 60 mg; 0.20 mmol) and thiomorpholine (0.20 mL; 2.0 mmol) to 250° C. under microwave irradiation according to the procedure described in Example 14 provided after purification by reverse phase HPLC, 1-methyl-5-thiomorpholin-4-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (15 mg, 21%) as light brown powder. ES-HRMS m/e calcd for C19H29N4OS4 (M+H+) 361.2057, found 361.2053.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 1-methyl-5-thiomorpholin-4-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (15 mg, 21%) as light brown powder

Sources & evidence

ORD record
ord-ab8f06c15335493f9ba9782a67a1932b
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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