Diisopropylethylamine → HCID 11429871, compound

HRID 859201Notes

Reaction equation

HRID 859201 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:20]([NH:29][CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][NH:32]2)[C:19]([C:36]([OH:38])=O)=[N:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]2[N:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[Cl:10])[N:18]=[C:19]3[C:20]=2[NH:29][CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:36]3=[O:38])=[CH:23][CH:24]=1

Participants

5

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 69451542HCID 69451542, compound

Product 1

HCID 11429871HCID 11429871, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (250 microliters, 2 mmol) was added to a mixture of 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-[(pyrrolidin-2-ylmethyl)-amino]-1H-pyrazole-3-carboxylic acid (I-5b, 160 mg, 0.37 mmol) and HATU (380 mg, 1 mmol) in DMF (50 ml) at room temperature. The reaction mixture was stirred for 5 hours, quenched with saturated aqueous NaCl, and extracted twice with EtOAc. The combined organic 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 in CH2Cl2 and the solvent decanted, a process repeated once more with EtOAc. The combined organic solutions were concentrated under vacuum and the residue was purified on a chromatogram using 4 mm plates and a solvent gradient of 10:1 EtOAc/MeOH to 5:1 EtOAc/MeOH to give 4A-1 as a white solid (46 mg): +ES MS (M+1) 413.4; 1H NMR (CD3OD) δ 7.58 (bs, 1H), 7.52–7.44 (m, 3H), 7.34 (d, 2H, J=7.6 Hz), 7.22 (d, 2H, J=7.6 Hz), 3.93–3.82 (m, 2H), 3.64–3.50 (m, 2H), 3.10–2.99 (m,1 H), 2.38–2.29 (m,1 H), 2.04–1.96 (m, 1H), 1.95–1.74 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-6cdf4e15422845b5a7888faad2209e8a
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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