Cyclopropylamine → HCID 57635941, compound

HRID 2109977Notes

Reaction equation

HRID 2109977 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13](Cl)[N:12]2[N:16]=[CH:17][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])=[C:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>C(O)C.CCOC(C)=O>[CH2:1]([S:8][C:9]1[N:14]=[C:13]([NH:28][CH:25]2[CH2:27][CH2:26]2)[N:12]2[N:16]=[CH:17][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])=[C:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 57635942HCID 57635942, compound

Product 1

HCID 57635941HCID 57635941, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound (5) and cyclopropylamine (1.2 g. 17.7 mmol) in anhydrous ethanol (10 mL) was stirred for 0.5 h at ambient temperature. The mixture was then diluted with EtOAc (200 mL), washed with saturated aqueous NaHCO3 and brine and dried over anhydrous Na2 SO4. Removal of the solvent provided 5-(2-benzylsulfanyl-4-cyclopropylamino-pyrazolo[1,5-a][1,3,5]triazin-8-yl)-pentanenitrile (6) (4.3 g. 65% in two steps).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried over anhydrous Na2 SO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-de48826d26894ee4b49698f4886463b2
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

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