HCID 86634631, compound → HCID 178523502, compound

HRID 1093722Notes

Reaction equation

HRID 1093722 reaction equation
C([O:8][C:9]1[CH:38]=[CH:37][CH:36]=[CH:35][C:10]=1[O:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:34])[CH2:19][NH:20][C:21]([C:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][N:24]=2)=[O:22])[CH2:14][CH2:13]1)C1C=CC=CC=1.Cl.C(OOC1C=CC=CC=1NC1CCNCC1)C1C=CC=CC=1>CO.O.[Pd]>[OH:8][C:9]1[CH:38]=[CH:37][CH:36]=[CH:35][C:10]=1[O:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18](=[O:34])[CH2:19][NH:20][C:21]([C:23]2[CH:27]=[C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:25][N:24]=2)=[O:22])[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 86634631HCID 86634631, compoundHCID 178523503HCID 178523503, compound

Product 1

HCID 178523502HCID 178523502, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

10% Pd/C (10 mg) was added to a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-benzyloxy-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (prepared from Intermediate 30 and (2-benzyloxyoxy-phenyl)-piperidin-4-yl-amine hydrochloride which was prepared according to the method used for the synthesis of Intermediate 15) (100 mg, 0.2 mmol) in a mixture of MeOH:H2O (1:1, 10 mL) under inert atmosphere and stirring was continued under H2 gas atmosphere for 2 hr. The reaction mixture was filtered through celite. The filtrate collected was concentrated under reduced pressure to afford the residue. The residue was purified by preparative HPLC to afford 60 mg (71.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-hydroxy-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 421.8, 96.21%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (b, 1H), 8.9 (b, 1H), 8.2 (b, 1H), 7.8 (m, 2H), 7.5 (m, 3H), 7.2 (s, 1H), 7.0 (d, 1H), 6.8 (m, 3H), 4.5 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.3 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).

Workup

  1. customwas prepared
  2. filtrationThe reaction mixture was filtered through celite
  3. customThe filtrate collected
  4. concentrationwas concentrated under reduced pressure
  5. customto afford the residue
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-88e2202d582847c48ef1468955053fdf
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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