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Dimethylformamide → 2-(6-Dimethylamino-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide

HRID 1879153
Notes
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Reaction equation

HRID 1879153 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](I)[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25](C)[CH:26]=O>ClCCl>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18]([N:25]([CH3:26])[CH3:24])[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 732132692-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 249547032-(6-Dimethylamino-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a sealed tube was added 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (See Example 2, 50 mg, 0.11 mmol, 1.0 equiv) and dimethyl formamide (1 mL). The reaction mixture was stirred at 100° C. After 18 hr, the reaction mixture was cooled to room temperature and diluted with dichloromethane washed with saturated NaHCO3, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to afford 2-(6-dimethylamino-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (32 mg, 80%). 1H NMR (400 MHz, CD2Cl2) δ 8.51 (s, 1H), 8.06 (s, 1H), 7.29-7.36 (m, 5H), 6.21 (bs, 1H), 4.59 (d, J=8.0 Hz, 2H), 3.17 (s, 6H), 2.71 (s, 3H); HRMS (M+H)+=354.13.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with saturated NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-a9fb413e86744b5989d1387a7ce940d3
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314138B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes