Diisopropylethylamine → HCID 66887009, compound

HRID 1631374Notes

Reaction equation

HRID 1631374 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.[F:49][C:50]1[CH:51]=[CH:52][C:53]([NH2:56])=[N:54][CH:55]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:49][C:50]1[CH:51]=[CH:52][C:53]([NH:56][C:22]([C:21]2[CH:20]=[N:19][N:16]3[CH:17]=[CH:18][C:13]([N:9]4[CH2:10][CH2:11][CH2:12][C@@H:8]4[C:4]4[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[N:14][C:15]=23)=[O:24])=[N:54][CH:55]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27377012-Amino-5-fluoropyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66847898HCID 66847898, compound

Product 1

HCID 66887009HCID 66887009, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a DMF (0.25 mL) solution of (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation I, 25 mg, 0.076 mmol) and HATU (35 mg, 0.092 mmol) was added 5-fluoropyridin-2-amine (10 mg, 0.092 mmol), followed by drop-wise addition of DIEA (0.040 mL, 0.23 mmol) at ambient temperature. The reaction was heated at 70° C. overnight, cooled, and directly purified by reverse-phase chromatography (5 to 66% acetonitrile/water) to yield the final product as white solid (25 mg, 78%). LCMS (apci) m/z=422.0 (M+H).

Workup

  1. temperaturecooled
  2. customdirectly purified by reverse-phase chromatography (5 to 66% acetonitrile/water)

Sources & evidence

ORD record
ord-117166a977e64289b75990e5a8ee2dc2
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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