Ethyl cyanoacetate → HCID 69813505, compound

HRID 1916137Notes

Reaction equation

HRID 1916137 reaction equation
O1CCCC1.[Br:6][C:7]1[C:8]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1.[C:44]([CH2:46][C:47](OCC)=[O:48])#[N:45]>O>[Br:6][C:7]1[C:8]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:47](=[O:48])[CH2:46][C:44]#[N:45])[CH2:17]2)=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8028TetrahydrofuranHCID 57346892DiazabicycloundecaneHCID 58177241(5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine

Product 1

HCID 69813505HCID 69813505, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A tetrahydrofuran solution (6 ml) of (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine (from Example 76, step 1 above) (300 mg, 0.99 mmol), diazabicycloundecane (530 mg, 3.5 mmol) and ethyl 2-cyanoacetate was stirred at room temperature for 20 hours. The reaction was diluted with water and extracted with ethyl acetate (2×). The organics were dried and evaporated to give 3-[(S)-3-(5-bromo-2-methylsulfanyl-pyrimidin-4-ylamino)-piperidin-1-yl]-3-oxo-propionitrile as an oil. MS (ES+): 371.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. customThe organics were dried
  3. customevaporated

Sources & evidence

ORD record
ord-da2b21f58e8f4a99bdd67587750059cc
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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