Cyclopropylamine → HCID 57785855, compound

HRID 1399197Notes

Reaction equation

HRID 1399197 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:18]3=[N:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH:27]([O:32][CH:33]([F:35])[F:34])[C:28]([F:31])([F:30])[F:29])[C:21]=4[N:17]3[CH2:16][CH2:15][CH2:14]2)=[C:9]([CH3:36])[N:8]=1)(=O)=O.[CH:39]1([NH2:42])[CH2:41][CH2:40]1>>[Cl:26][C:25]1[C:20]2[N:19]=[C:18]3[N:13]([C:10]4[CH:11]=[CH:12][C:7]([NH:42][CH:39]5[CH2:41][CH2:40]5)=[N:8][C:9]=4[CH3:36])[CH2:14][CH2:15][CH2:16][N:17]3[C:21]=2[C:22]([CH:27]([O:32][CH:33]([F:35])[F:34])[C:28]([F:29])([F:30])[F:31])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 57785992HCID 57785992, compound

Product 1

HCID 57785855HCID 57785855, compoundYield 42%

Conditions

Temperature
60 °C

Procedure

A mixture of 5-{9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl}-6-methylpyridin-2-yl trifluoromethanesulfonate (130.4 mg, 0.219 mmol) and cyclopropylamine (2.0 mL) was stirred at 60° C. for 25.5 hrs. The reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-60% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from ethyl acetate/n-hexane to give a title compound as a colorless powder (45.6 mg, 0.909 mmol, 42%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with a 10-60% ethyl acetate/n-hexane gradient mixture
  4. customThe resulting solid was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e83de45ac38e461faadd24fde8578992
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…