HCID 71253388, compound → HCID 67456006, compound

HRID 571106Notes

Reaction equation

HRID 571106 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=[O:23])[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(Cl)Cl.CO.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=[O:23])[CH:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 71253388HCID 71253388, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67456006HCID 67456006, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of the urea product, obtained above, (130 mg, 0.32 mmol) in DCM/MeOH (1:1 v/v, 40 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 25° C., 70 mm, 10% Pt/C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo. The residue was partitioned between DCM (10 mL) and sat. aq NaHCO3 and the organic layer was separated and washed with brine (10 mL), dried and evaporated in vacuo to afford the title compound, Intermediate D6, as a red solid (87 mg, 69%); Rt 1.05 min (Method 2); m/z 378 (M+H)+ (ES+).

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was partitioned between DCM (10 mL) and sat. aq NaHCO3
  3. customthe organic layer was separated
  4. washwashed with brine (10 mL)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-59c50ee3a45e424995a93e743f5399be
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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