Propanal → HCID 68027530, compound

HRID 527899Notes

Reaction equation

HRID 527899 reaction equation
Cl.[N:2]1[C:7]2[NH:8][CH:9]=[CH:10][C:6]=2[C:5]([N:11]2[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]2)=[N:4][CH:3]=1.[CH:17](=O)[CH2:18][CH3:19]>C1COCC1>[CH2:17]([NH:16][C@@H:13]1[CH2:14][CH2:15][N:11]([C:5]2[C:6]3[CH:10]=[CH:9][NH:8][C:7]=3[N:2]=[CH:3][N:4]=2)[CH2:12]1)[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 527PropanalHCID 86692135HCID 86692135, compound

Product 1

HCID 68027530HCID 68027530, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine hydrochloride (50 mg, 0.24 mmol), propionaldehyde (15 mg, 0.26 mmol) and NaBH(OAC)3 (61 mg, 1.2 mmol) in THF (5 mL) was stirred at the ambient temperature for minutes. It was then quenched with water (2 mL) and extracted with EtOAc (3×10 mL). The combined extracts were washed with brine (3×5 mL), dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound. MS (m/z): 246 (M+H)+.

Workup

  1. customIt was then quenched with water (2 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined extracts were washed with brine (3×5 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13bf79720b0c45e29ef0f35cb94eaefc
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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