HCID 89662746, compound → HCID 131736561, compound

HRID 1479102Notes

Reaction equation

HRID 1479102 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH:24]([CH3:27])[CH2:25][OH:26])=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:28]>C(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH:24]([CH3:27])[CH:25]=[O:26])=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:28]

Participants

3

Reactant 1

HCID 89662746HCID 89662746, compound

Product 1

HCID 131736561HCID 131736561, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DMP (291 mg; 0.69 mmol; 1.25 eq.) was added at 0° C. to a solution of Example 143 (220 mg; 0.55 mmol; 1 eq.) in DCM (10 mL) and the reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with DCM, washed with sat. aq. NaHCO3 then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (25% to 65% EA in cyclohexane) afforded the title compound (170 mg, 78%) as a white solid. UPLC/MS: (MS+) 399.1 ([M+H]+).

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (25% to 65% EA in cyclohexane)

Sources & evidence

ORD record
ord-18cb6615d4144c328b98eaad0a897292
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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