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Diisopropylethylamine → HCID 178434563, compound

HRID 522079
Notes
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Reaction equation

HRID 522079 reaction equation
CN(C(O[N:9]1[N:17]=[N:16][C:11]2[CH:12]=[CH:13]C=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:48]=[CH:47][C:46]([C:49]2[C:54]([F:55])=[CH:53][CH:52]=[CH:51][N:50]=2)=[CH:45][C:27]=1[C:28]([NH:30][C:31]1[N:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:34]=[C:33]([C:42](O)=[O:43])[CH:32]=1)=[O:29].CCN(C(C)C)C(C)C.CC1C(N)=CNN=1>CN(C=O)C.CCOC(C)=O>[Cl:25][C:26]1[CH:48]=[CH:47][C:46]([C:49]2[C:54]([F:55])=[CH:53][CH:52]=[CH:51][N:50]=2)=[CH:45][C:27]=1[C:28]([NH:30][C:31]1[N:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:34]=[C:33]([C:42]([NH:16][C:11]2[C:12]([CH3:13])=[N:17][NH:9][CH:10]=2)=[O:43])[CH:32]=1)=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1184971095-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidHCID 178434557HCID 178434557, compound

Product 1

HCID 178434563
HCID 178434563, compound
Yield 29.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of HATU (0.3 mmol, 113 mg) and 5-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 105, 0.23 mmol, 100 mg) in DMF (0.9 mL) was added DIPEA (1.10 mmol, 0.191 mL). The solution was stirred at room temperature for 15 minutes. 3-methyl-1H-pyrazol-4-amine (0.23 mmol, 100 mg) was added and the reaction stirred at room temperature for 18 hours. The reaction was diluted with EtOAc (20 mL), washed with NaHCO3 (20 mL), 10% aqueous citric acid solution (20 mL) and brine (20 mL). The organic layer was dried over sodium sulphate and concentrated in vacuo. The residue was purified using reverse phase column chromatography to afford the title compound as a yellow solid (35 mg, 29%).

Workup

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. washwashed with NaHCO3 (20 mL), 10% aqueous citric acid solution (20 mL) and brine (20 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-b079327898c0470c86cfb8b5e3eb952a
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328096B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes