Diisopropylethylamine → HCID 67500744, compound

HRID 1631369Notes

Reaction equation

HRID 1631369 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=[N:40][C:35]2[CH:36]=[CH:37]C=N[C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CC1(N)CC1.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:40][C:35]4([CH3:34])[CH2:37][CH2:36]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 12953687(1-Methylcyclopropyl)amine hydrochlorideHCID 66847898HCID 66847898, compound

Product 1

HCID 67500744HCID 67500744, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (0.6 mL) solution of (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation I, 10.5 mg, 0.0321 mmol) and HATU (14.6 mg, 0.0385 mmol) was added 1-methylcyclopropanamine hydrochloride (4.14 mg, 0.0385 mmol) and DIEA (0.0168 mL, 0.0962 mmol). After stirring for 10 minutes, the reaction mixture was directly purified by reverse-phase chromatography (5 to 50% acetonitrile/water) to yield the final product as white solid (10 mg, 82%). LCMS (apci) m/z=381.1 (M+H).

Workup

  1. customthe reaction mixture was directly purified by reverse-phase chromatography (5 to 50% acetonitrile/water)

Sources & evidence

ORD record
ord-b4bc8da7895f497bb9c9a1d4ebca1eaa
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

Loading…