Ammonia → HCID 178503058, compound

HRID 41872Notes

Reaction equation

HRID 41872 reaction equation
C[N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:26][CH3:27])[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]2[C@H:28]3[CH2:33][CH2:32][CH2:31][C@H:29]3[N:30]=[C:3]12.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.N>CO>[CH3:27][S:26][C:9]1[N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=3)=[CH:15][CH:14]=2)[N:11]=[C:5]2[N:4]3[C@H:28]4[CH2:33][CH2:32][CH2:31][C@H:29]4[N:30]=[C:3]3[NH:2][C:7](=[O:8])[C:6]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14817Phosphorus sulfide (P2S5)HCID 58456641HCID 58456641, compound

Product 1

HCID 178503058HCID 178503058, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(methylthio)-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (25 mg, 0.054 mmol) and P4S10 (48.1 mg, 0.108 mmol) are placed in a Biotage microwave vial, and then 1.0 mL of 7N ammonia in MeOH is added. The sealed vial is heated in a Biotage microwave at 150° C. for 6 h. After solvent is removed, the residue is suspended in DMF, and then filtered. The obtained filtrate is purified by a semi-preparative HPLC to give 10.6 mg of pure product as pale yellow solids (yield: 44%). MS (ESI) m/z 449.2 [M+H]+.

Workup

  1. customAfter solvent is removed
  2. filtrationfiltered
  3. customThe obtained filtrate is purified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-36ad0d15757644df8a70ab716eacc39d
Source dataset
uspto-grants-2013_09
Patent number
US08536159B2

Reaction notes

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