Diisopropylethylamine → HCID 70170025, compound

HRID 1426970Notes

Reaction equation

HRID 1426970 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][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.C(N(C(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)[CH2:4][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 67471034HCID 67471034, compound

Product 1

HCID 70170025HCID 70170025, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (R)-5-(2-(2-(3-aminopropyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (16 mg, 0.042 mmol) in DMF (5 mL) was added HATU (63 mg, 0.17 mmol) and N-ethyl-N-isopropylpropan-2-amine (22 mg, 0.17 mmol). The reaction mixture was stirred for 3 hours and concentrated under reduced pressure. The crude residue was purified by silica column chromatography using 100% EtOAc to afford the title compound (6.0 mg, 39% yield). MS (apci) m/z=367.3 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-f343135f5470411db5fdbda29527175f
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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