Cyclopropylamine → HCID 68029031, compound

HRID 527940Notes

Reaction equation

HRID 527940 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:25])[C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.[CH:26]1([NH2:29])[CH2:28][CH2:27]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:25])[C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH:29][CH:26]4[CH2:28][CH2:27]4)=[O:21])=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68029369HCID 68029369, compound

Product 1

HCID 68029031HCID 68029031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-6-((1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)(methyl)amino)nicotinic acid (33.8 mg, 0.1 mmol) in DMF (2 mL) were added cyclopropylamine (5.71 mg, 0.2 mmol), DIPEA (26 mg, 0.2 mmol) and HATU (38.0 mg, 0.1 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The volatiles were removed under reduced pressure and the residue was purified by silica gel chromatography to give the title compound. MS (m/z): 378 (M+H)+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ecc9d24b1dfb4d0797d58e948210758e
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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