Dichloromethane → HCID 86676747, compound

HRID 571105Notes

Reaction equation

HRID 571105 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][O:27][CH2:26][CH2:25]3)=[O:23])[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.C(Cl)Cl.[H][H]>CO.CC(O)=O.[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[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])[CH:16]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 71253070HCID 71253070, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86676747HCID 86676747, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-((4-nitronaphthalen-1-yl)oxy)pyridin-2-yl)morpholine-4-carboxamide (900 mg, 2.3 mmol) in a mixture of MeOH (140 mL), DCM (140 mL) and AcOH (4 drops) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 25° C., 55 mm, 10% Pt—C Cat-Cart, full hydrogen mode). The reaction mixture was evaporated in vacuo and the residue was partitioned between DCM (50 mL) and saturated aq. NaHCO3 (20 mL). The organic phase was separated and was washed with brine (20 mL), and then dried and evaporated in vacuo to afford the title compound, Intermediate D5, as a brown solid (0.78 g, 90%); Rt 3.65 min (Method 1 basic); m/z 365 (M+H)+ (ES+).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between DCM (50 mL) and saturated aq. NaHCO3 (20 mL)
  3. customThe organic phase was separated
  4. washwas washed with brine (20 mL)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-eef468fab8f54c13b584e14f1a2b648d
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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