Triethylamine → 2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-N-(1-methyl-1-phenylethyl)-1,3-thiazole-5-carboxamide

HRID 2243050Notes

Reaction equation

HRID 2243050 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([NH:27][C:28]([NH:30][C:31]1[N:36]=[CH:35][C:34]([C:37]2[S:38][C:39]([C:42]([OH:44])=O)=[CH:40][N:41]=2)=[CH:33][CH:32]=1)=[O:29])[CH3:26].CCN(CC)CC.[C:52]([NH2:61])([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)([CH3:54])[CH3:53]>CN(C=O)C.O>[CH2:25]([NH:27][C:28]([NH:30][C:31]1[N:36]=[CH:35][C:34]([C:37]2[S:38][C:39]([C:42]([NH:61][C:52]([CH3:54])([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH3:53])=[O:44])=[CH:40][N:41]=2)=[CH:33][CH:32]=1)=[O:29])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 251261342-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 592084552-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-N-(1-methyl-1-phenylethyl)-1,3-thiazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (0.078 mg, 0.225 mmol) was added to a solution of 2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (Example 17, 60 mg, 0.205 mmol), Et3N (84 μL, 0.41 mmol) and cumylamine (28 mg, 0.205 mmol) in 3 mL DMF. After stirring at room temperature for two hours, the mixture was diluted with water and extracted with EtOAc. The product precipitated during the workup and it was collected by filtration, washed with water and EtOAc and dried (20 mg). MS (ESP): 410 (M+H+) for C21H23N5O2S.

Workup

  1. extractionextracted with EtOAc
  2. customThe product precipitated during the workup and it
  3. filtrationwas collected by filtration
  4. washwashed with water and EtOAc
  5. customdried (20 mg)

Sources & evidence

ORD record
ord-409de890c2584456b9e4a1b949e4c50c
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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