Methanol → HCID 46244939, compound

HRID 1846556Notes

Reaction equation

HRID 1846556 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]2[NH:7][C:8](=[O:35])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([O:24][C:25]5[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[C:27]([CH3:34])[CH:26]=5)[N:21]=[CH:20][N:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.CO.[H][H]>C1COCC1.[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][C:22]2[N:21]=[CH:20][N:19]=[C:18]([N:15]3[CH2:14][CH2:13][CH:12]([N:9]4[CH2:10][CH2:11][C:5]5[CH:4]=[C:3]([O:2][CH3:1])[CH:37]=[CH:36][C:6]=5[NH:7][C:8]4=[O:35])[CH2:17][CH2:16]3)[CH:23]=2)=[CH:26][C:27]=1[CH3:34]

Participants

6

Reactant 3

HCID 887MethanolHCID 66978230HCID 66978230, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 46244939HCID 46244939, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

930 mg (1.84 mmol) 7-methoxy-3-(1-(6-(3-methyl-4-nitrophenoxy)pyrimidin-4-yl)piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one were placed in 20 mL THF and 20 mL MeOH and hydrogenated under a hydrogen atmosphere with the addition of 150 mg Pd/C (10%) at RT and a hydrogen pressure of 3 bar until all the hydrogen had been taken up. The catalyst was filtered off. Everything was distilled off from the filtrate to leave a residual volume of 15 mL. DIPE was added. The precipitate was suction filtered, washed and dried.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationEverything was distilled off from the filtrate
  3. customto leave a residual volume of 15 mL
  4. additionDIPE was added
  5. filtrationfiltered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-4b9e75d9d13345418cbabcb89d98ff45
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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