Diisopropylethylamine → HCID 70169441, compound

HRID 1426924Notes

Reaction equation

HRID 1426924 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]2[CH:21]=[CH:20][N:19]3[N:22]=[CH:23][C:24]([C:25]([OH:27])=O)=[C:18]3[N:17]=2)=[CH:9][C:8]([F:28])=[CH:7][N:6]=1.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:28][C:8]1[CH:9]=[C:10]2[C:5](=[N:6][CH:7]=1)[NH:4][CH2:3][CH2:2][NH:1][C:25](=[O:27])[C:24]1=[C:18]3[N:17]=[C:16]([CH:21]=[CH:20][N:19]3[N:22]=[CH:23]1)[N:12]1[C@@H:11]2[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67471029HCID 67471029, compound

Product 1

HCID 70169441HCID 70169441, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (3 mL) solution of (R)-5-(2-(2-(2-aminoethylamino)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (25 mg, 0.065 mmol) was first added HATU (29 mg, 0.077 mmol), followed by five-minute stirring and then drop-wise addition of DIEA (56 μL, 0.32 mmol). After stirring at ambient temperature overnight, the reaction was directly purified by reverse phase column chromatography (Biotage SP4 system C18 25+M cartridge, acetonitrile/water 5 to 45%), to yield the title product as off-white solid (7 mg, 30% yield). MS (apci) m/z=368.2 (M+H).

Workup

  1. customthe reaction was directly purified by reverse phase column chromatography (Biotage SP4 system C18 25+M cartridge, acetonitrile/water 5 to 45%)

Sources & evidence

ORD record
ord-4cc6930f8aca479aa7df28877262cfa9
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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