Cyanoacetic acid → HCID 56836181, compound

HRID 527910Notes

Reaction equation

HRID 527910 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH:16]=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:4]1.[C:17]([CH2:19][C:20]([OH:22])=O)#[N:18].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>C1COCC1>[N:11]1[C:10]2[NH:14][CH:15]=[CH:16][C:9]=2[C:8]([N:5]2[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:1])[C:20](=[O:22])[CH2:19][C:17]#[N:18])[CH2:4]2)=[N:13][CH:12]=1

Participants

6

Reactant 4

HCID 9740Cyanoacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68027120HCID 68027120, compound

Product 1

HCID 56836181HCID 56836181, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)—N-methyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine (75 mg, 0.345 mmol) and 2-cyanoacetic acid (35 mg, 0.414 mmol) in THF (5 mL) were added HATU (157 mg, 0.414 mmol) and DIPEA (0.12 mL, 0.69 mmol). The reaction mixture was stirred at room temperature for 20 hours. The precipitate was filtered, washed with EtOAc, and dried under reduced pressure to give the title compound (45 mg, 46%). MS (m/z): 285 (M+H)+.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with EtOAc
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-67ee64df3d3946fa9b71044c4289d7bc
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

Loading…