HCID 178428671, compound → HCID 178428672, compound

HRID 473865Notes

Reaction equation

HRID 473865 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([NH:26]CC5C=CC=CC=5)[NH:23][N:22]=4)[CH:19]=[CH:20][C:14]=3[O:13][CH2:12][CH2:11]2)=[O:9])[CH2:4][CH2:3]1>[Pd].CO>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([NH2:26])[NH:23][N:22]=4)[CH:19]=[CH:20][C:14]=3[O:13][CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 178428671HCID 178428671, compound

Product 1

HCID 178428672HCID 178428672, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-{4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-N-(phenylmethyl)-1H-pyrazol-5-amine (example 6) (39 mg, 0.088 mmol), 10% palladium on charcoal (37 mg) and methanol (15 mL) was hydrogenated in a Parr apparatus at 45 psi for 18 hours. The suspension was filtered, concentrated and the residue purified by preparative reverse phase HPLC to give 3-{4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-1H-pyrazol-5-amine (17 mg, 55% yield). 1H NMR (400 MHz, methanol-d4): 7.50 (br, 1H), 7.46 (dd, 1H), 6.98 (d, 1H), 5.86 (s, 1H), 4.44 (s, 2H), 4.18 (m, 2H), 3.68 to 3.60 (m, 4H), 2.80 (t, 2H), 1.67 to 1.51 (m, 3H), 1.23 to 1.15 (m, 2H), 0.97 (d, 2H); MS (EI) for C19H25N5O2: 356 (MH+).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationconcentrated
  3. customthe residue purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-e8cbfb6afe5e466db3abcc1c6b9f55c3
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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