Diisopropylethylamine → HCID 67502183, compound

HRID 1631396Notes

Reaction equation

HRID 1631396 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][C@@H:10]([CH2:13][OH:14])[N:9]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([OH:26])=O)=[C:17]3[N:16]=2)[CH:5]=[N:6][CH:7]=1.[F:27][C:28]([F:33])([F:32])[C@H:29]([NH2:31])[CH3:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][C@@H:10]([CH2:13][OH:14])[N:9]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([NH:31][C@H:29]([CH3:30])[C:28]([F:33])([F:32])[F:27])=[O:26])=[C:17]3[N:16]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

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 10964446(2R)-1,1,1-Trifluoro-2-propanamineHCID 66848138HCID 66848138, compound

Product 1

HCID 67502183HCID 67502183, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-((2R,5S)-2-(5-fluoropyridin-3-yl)-5-(hydroxymethyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (10.0 mg, 0.028 mmol), (R)-1,1,1-trifluoropropan-2-amine (6.33 mg, 0.056 mmol) and HATU (10.5 mg, 0.045 mmol) in dry DMF (0.2 mL) was added DIEA (15.0 μL, 0.084 mmol). The reaction vessel was flushed with nitrogen, sealed, and the reaction stirred at ambient temperature for 16 hours. The reaction mixture was directly purified by reverse phase column chromatography (0-50% CH3CN/H2O) to provide the title compound (6.50 mg, 51% yield) as a white solid. MS (apci) m/z=453.0 (M+H).

Workup

  1. customThe reaction vessel was flushed with nitrogen
  2. customsealed
  3. customThe reaction mixture was directly purified by reverse phase column chromatography (0-50% CH3CN/H2O)

Sources & evidence

ORD record
ord-bea7dfff313940ceaa4ad4fdbe5a17f9
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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