1,2-Dichloroethane → HCID 67431798, compound

HRID 410618Notes

Reaction equation

HRID 410618 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3([C:27](O)=[O:28])[CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[CH:30]([NH:32][NH2:33])=[O:31].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH:30]([NH:32][NH:33][C:27]([C:24]1([C:22]2[S:23][C:19]([C:4]3[CH:5]=[C:6]([NH:8][C:9]4[N:14]=[C:13]([C:15]([F:16])([F:18])[F:17])[CH:12]=[CH:11][N:10]=4)[CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:20][N:21]=2)[CH2:25][CH2:26]1)=[O:28])=[O:31]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 12229HydrazinecarboxaldehydeHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58456358HCID 58456358, compound

Product 1

HCID 67431798HCID 67431798, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-[5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclopropanecarboxylic acid (TFA salt, 110 mg, 0.206 mmol), formic acid hydrazide (37 mg, 0.617 mmol), HOBT (95 mg, 0.617 mmol), and EDC (118 mg, 0.617 mmol) were combined with DMF (5 mL) and DIEA (80 mg, 0.617 mmol). The reaction was stirred for 3 h at room temperature. It was subsequently diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. The residue was triturated with ether and filtered to provide N′-formyl-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclopropanecarbohydrazide (88 mg, 92%) as a colorless solid. MS ESI: [M+H]+ m/z 463.0.

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
  6. customThe residue was triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-3ccc48378ad44ea9a7bfaa40375ad1fa
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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