Diisopropylethylamine → Methyl 2-[({1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-thiazole-5-carboxylate

HRID 222369

Reaction equation

HRID 222369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([OH:17])=O)[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:18][C:19]1[S:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([NH:18][C:19]3[S:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 238005Methyl 2-aminothiazole-5-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595836511-(3,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid2×

Product 1

HCID 59583664Methyl 2-[({1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-thiazole-5-carboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylic acid (Intermediate 11) (1 g, 3.6 mmol), methyl 2-amino-1,3-thiazole-5-carboxylate (0.58 g, 3.6 mmol), HATU (1.82 g, 1.3 eq) and DIPEA (0.9 mL, 1.3 eq) in DMF (50 mL) was stirred at 40° C. for 3 days. The solvent was evaporated and the residue was washed with water and extracted with DCM. A precipitate was formed, filtered and triturated with a mixture of methanol/acetonitrile. After filtration, the yellow solid was dried to give the title compound as a pale yellow solid (644 mg, 44%). LC/MS: m/z 412 (M+H)+. Rt: 3.21 min.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with DCM
  4. customA precipitate was formed
  5. filtrationfiltered
  6. customtriturated with a mixture of methanol/acetonitrile
  7. filtrationAfter filtration
  8. customthe yellow solid was dried

Sources & evidence

ORD record
ord-0e4dd81a0f604d5abbc3277d61d9af30
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Linked notes

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