HCID 66978307, compound → HCID 178487202, compound

HRID 1846562Notes

Reaction equation

HRID 1846562 reaction equation
Cl[C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:31][CH2:30][C:29]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:28]=4[NH:27][C:26]3=[O:38])[CH2:21][CH2:20]2)[CH:14]=1.[H][H]>CO.[Pd]>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:28]2[NH:27][C:26](=[O:38])[N:25]([CH:22]3[CH2:23][CH2:24][N:19]([C:15]4[CH:14]=[C:13]([O:12][C:3]5[CH:4]=[CH:5][C:6]6[NH:7][C:8]([CH3:11])=[N:9][C:10]=6[CH:2]=5)[N:18]=[CH:17][N:16]=4)[CH2:20][CH2:21]3)[CH2:31][CH2:30][C:29]=2[CH:32]=1

Participants

5

Reactant 2

HCID 66978307HCID 66978307, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 178487202HCID 178487202, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

90 mg (0.17 mmol) 3-(1-(6-(4-chloro-2-methyl-1H-benzo[d]imidazol-5-yloxy)pyrimidin-4-yl)piperidin-4-yl)-7-methoxy-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one and 0.10 mL (0.71 mmol) TEA were placed in 10 mL methanol and hydrogenated under hydrogen atmosphere and with the addition of 10 mg Pd/C (10%) at 50° C. and a hydrogen pressure of 3 bar until the uptake of hydrogen had ended. The catalyst was filtered off and the filtrate was evaporated down i.vac. The residue was purified by preparative HPLC-MS. The fractions containing product were combined and freeze-dried.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down i.vac
  3. customThe residue was purified by preparative HPLC-MS
  4. additionThe fractions containing product
  5. customfreeze-dried

Sources & evidence

ORD record
ord-c835be16fcd148699e9b6a5978e3003e
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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