HCID 86672028, compound → HCID 49833507, compound

HRID 473879Notes

Reaction equation

HRID 473879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][C:13](=[O:15])[CH2:12][CH2:11][N:10]2[C:16]([N:18]2[CH2:24][C:23]3[CH:25]=[C:26]([C:29]4[CH:30]=[CH:31][C:32]5[N:36]=[C:35]([NH:37]C(=O)OCC6C=CC=CC=6)[NH:34][C:33]=5[CH:48]=4)[CH:27]=[CH:28][C:22]=3[O:21][CH2:20][CH2:19]2)=[O:17])[CH:5]=[CH:6][C:7]=1[F:8]>C(O)(=O)C.[Pd]>[NH2:37][C:35]1[NH:34][C:33]2[CH:48]=[C:29]([C:26]3[CH:27]=[CH:28][C:22]4[O:21][CH2:20][CH2:19][N:18]([C:16]([N:10]5[CH2:11][CH2:12][C:13](=[O:15])[CH2:14][CH:9]5[C:4]5[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=5)=[O:17])[CH2:24][C:23]=4[CH:25]=3)[CH:30]=[CH:31][C:32]=2[N:36]=1

Participants

4

Reactant 1

HCID 86672028HCID 86672028, compound

Product 1

HCID 49833507HCID 49833507, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of phenylmethyl [6-(4-{[2-(3,4-difluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazol-2-yl]carbamate (0.11 g, 0.17 mmol) in acetic acid (5 mL) was hydrogenated at 1 atm over 10% Pd—C (0.1 g) for 2 h. The catalyst was filtered off and the filtrate was concentrated. The resulting brown residue was dissolved in methanol and purified by preparative reverse phase HPLC to afford 1-{[7-(2-amino-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]carbonyl}-2-(3,4-difluorophenyl)piperidin-4-one (0.007 g, 8% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3): 7.02-7.29 (m, 8H), 6.98 (d, 1H), 6.94 (d, 1H), 5.27 (t, 1H), 4.43-4.46 (m, 2H), 4.16-4.30 (m, 2H), 3.70-3.85 (m, 3H), 3.21-3.31 (m, 1H), 2.79-2.99 (m, 2H), 2.51-2.61 (m, 1H), 2.32 (d, 1H); MS (EI) for C28H25F2N5O3: 518 (MH+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe resulting brown residue was dissolved in methanol
  4. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-dd4401be5c434aae9da64dc5162ef5ad
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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