Dimethylformamide → HCID 178451667, compound

HRID 13346

Reaction equation

HRID 13346 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[N:2]1.CN(C)C=O.[NH2:13][C:14]1[C:19]([NH2:20])=[CH:18][C:17]([CH:21]2[CH2:25][CH2:24][CH2:23][N:22]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:16]([O:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=2)[CH:15]=1>C(OCC)(=O)C>[CH3:43][S:40]([C:37]1[CH:38]=[CH:39][C:34]([O:33][C:16]2[C:17]([CH:21]3[CH2:25][CH2:24][CH2:23][N:22]3[C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])=[CH:18][C:19]3[NH:20][C:6]([C:3]4[CH:4]=[CH:5][NH:1][N:2]=4)=[N:13][C:14]=3[CH:15]=2)=[CH:35][CH:36]=1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 122183831H-Pyrazole-3-carbaldehydeHCID 23145168t-Butyl 2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)phenyl)-pyrrolidine-1-carboxylate

Product 1

HCID 178451667HCID 178451667, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

10.0 mg of 1H-pyrazole-3-carboxaldehyde was added to an N,N-dimethylformamide (1 ml) solution of 49.0 mg of t-butyl 2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)-phenyl)-pyrrolidine-1-carboxylate obtained in Example 306 (step 3), and the reaction liquid was stirred overnight at 90° C. After cooled, the reaction liquid was diluted with ethyl acetate, washed with saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as a brown solid.

Workup

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. customthe reaction liquid
  4. washwashed with saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified
  8. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-e88808f8ef4a4eb29b06851b1f3a5734
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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