1,2-Dichloroethane → HCID 67433005, compound

HRID 410608Notes

Reaction equation

HRID 410608 reaction equation
[CH3:1][C:2]([CH3:30])([CH2:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][N:20]=3)[CH:15]=[C:14]([CH3:29])[CH:13]=2)=[CH:10][N:11]=1)[C:3]([OH:5])=O.[CH:31]([NH:33][NH2:34])=[O:32].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH:31]([NH:33][NH:34][C:3](=[O:5])[C:2]([CH3:1])([CH3:30])[CH2:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[N:24]=[C:23]([C:25]([F:27])([F:28])[F:26])[CH:22]=[CH:21][N:20]=3)[CH:15]=[C:14]([CH3:29])[CH:13]=2)=[CH:10][N:11]=1)=[O:32]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 12229HydrazinecarboxaldehydeHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58456383HCID 58456383, compound

Product 1

HCID 67433005HCID 67433005, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,2-Dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propanoic acid (potassium salt) (87% pure, 100 mg, 0.183 mmol), formic acid hydrazide (22.0 mg, 0.367 mmol), HOBT (56.2 mg, 0.367 mmol), and EDC (70.3 mg, 0.367 mmol) were combined with DMF (4 mL) and DIEA (47.4 mg, 0.367 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Flash chromatography (0-10% methanol in ethyl acetate) afforded N′-formyl-2,2-dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propanehydrazide (70 mg, 80%) as a yellow gum. ESI: [M+H]+ m/z 479.0.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-39e8cf729f274e37be24b35f2f03664b
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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