HCID 178523761, compound → HCID 178519698, compound

HRID 1914635Notes

Reaction equation

HRID 1914635 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][N:16]=2)[CH2:9][CH2:8]1)=[O:5]>[O-2].[Mn+4].[O-2].C(Cl)Cl>[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][N:16]=2)[CH2:11][CH2:12]1)=[O:5]

Participants

4

Reactant 1

HCID 178523761HCID 178523761, compound

Product 1

HCID 178519698HCID 178519698, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Trans-2-Chloro-N-{-4-[(5-hydroxymethyl-pyridin-2-ylamino)-methyl]-cyclohexyl}-5-trifluoromethyl-benzamide (Example 19.20) (100 mg, 0.23 mmol) is placed in a flask with DCM (10 mL) and manganese (IV) oxide (297 mg, 3.4 mmol). The reaction mixture is stirred at RT for 4 hours and manganese (IV) oxide is removed by filtration. The solvent was removed in vacuo to afford the title compound; NMR (400 MHz, DMSO-d6) δ 9.66 (1H, s), 8.49 (2H, m), 7.77 (5H, m), 6.58 (1H, d), 3.70 (1H, m), 3.23 (2H, m), 1.93 (2H, m), 1.81 (2H, m), 1.53 (1H, m), 1.23 (2H, m), 1.09 (2H, m).

Workup

  1. custommanganese (IV) oxide is removed by filtration
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-29ea68f1866c48fd9117af50cdd92695
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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