Diisopropylethylamine → HCID 58763927, compound

HRID 859194Notes

Reaction equation

HRID 859194 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:15]([C:33](O)=[O:34])=[N:16][N:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Na+].[Cl-]>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[N:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])[N:16]=[C:15]3[C:33](=[O:34])[NH:10][CH2:11][CH2:12][NH:13][C:14]=23)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58763949HCID 58763949, compound

Product 1

HCID 58763927HCID 58763927, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (209 microliters, 1.2 mmol) was added slowly via syringe to a solution of 4-(2-aminoethylamino)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid (I-4d, 228 mg, 0.53 mmol) and HATU (456 mg, 1.2 mmol) in anhydrous DMF (30 ml) at room temperature. The reaction mixture was stirred for 17 hours, diluted with saturated aqueous NaCl, and extracted with EtOAc (2×). The combined EtOAc extracts were washed with 0.5 M citric acid, 1 M K2CO3, and saturated aqueous NaCl, dried and concentrated in vacuo. The residue was slurried with CH2Cl2 and the organic solvent decanted, a process that was repeated twice. The combined organic solutions were concentrated in vacuo and the residue was purified on a chromatotron using 4 mm plates and a solvent gradient of 100% EtOAc to 10:1 EtOAC/MeOH to give I-4e as a colorless solid (82 mg): +ES MS (M+1) 373.4.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined EtOAc extracts were washed with 0.5 M citric acid, 1 M K2CO3, and saturated aqueous NaCl
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customthe organic solvent decanted
  6. concentrationThe combined organic solutions were concentrated in vacuo
  7. customthe residue was purified on a chromatotron

Sources & evidence

ORD record
ord-12accc6f3c2949f08159fe7c6b8330fa
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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