Diisopropylethylamine → HCID 67501160, compound

HRID 1631378Notes

Reaction equation

HRID 1631378 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([OH:24])=O)=[C:15]3[N:14]=2)[CH:5]=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[F:50][C:51]([F:57])([F:56])[C:52]1([NH2:55])[CH2:54][CH2:53]1.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][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([NH:55][C:52]4([C:51]([F:57])([F:56])[F:50])[CH2:54][CH2:53]4)=[O:24])=[C:15]3[N:14]=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 116511961-(Trifluoromethyl)cyclopropanamine hydrochlorideHCID 66847898HCID 66847898, compound

Product 1

HCID 67501160HCID 67501160, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (0.4 mL) solution of (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation I, 50 mg, 0.15 mmol) and HATU (87 mg, 0.23 mmol) was charged 1-(trifluoromethyl)cyclopropanamine hydrochloride (37 mg, 0.23 mmol), followed by drop-wise addition of DIEA (0.080 mL, 0.46 mmol). After stirring first at ambient temperature for 15 minutes and then at 85° C. overnight, the reaction was cooled and directly purified by reverse-phase chromatography (5 to 60% acetonitrile/water) to yield the final product as off-white solid (15 mg, 23%). LCMS (apci) m/z=435.0 (M+H).

Workup

  1. temperatureat 85° C. overnight, the reaction was cooled
  2. customdirectly purified by reverse-phase chromatography (5 to 60% acetonitrile/water)

Sources & evidence

ORD record
ord-61a57141a7a64ff78100d1ae9da2ef3c
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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