4-(2-Oxo-1,4-dihydro-2h-quinazolin-3-yl)-piperidine-1-carboxylic acid[1-(6-benzyloxy-pyridin-3-ylmethyl)-2-[1,4']bipiperidinyl-1'-yl-2-oxo-ethyl]-amide → (+/-)-4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid [2-[1,4']bipiperidinyl-1'-yl-2-oxo-1-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-ethyl]-amide

HRID 1177751Notes

Reaction equation

HRID 1177751 reaction equation
C([O:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:31][C:32]([N:34]2[CH2:39][CH2:38][CH:37]([N:40]3[CH2:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[NH:42][C:41]3=[O:50])[CH2:36][CH2:35]2)=[O:33])[C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:21][CH2:20]2)=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[N:25]1([CH:22]2[CH2:21][CH2:20][N:19]([C:17](=[O:18])[CH:16]([NH:31][C:32]([N:34]3[CH2:35][CH2:36][CH:37]([N:40]4[CH2:49][C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[NH:42][C:41]4=[O:50])[CH2:38][CH2:39]3)=[O:33])[CH2:15][C:12]3[CH:11]=[CH:10][C:9](=[O:8])[NH:14][CH:13]=3)[CH2:24][CH2:23]2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 1

HCID 100097694-(2-Oxo-1,4-dihydro-2h-quinazolin-3-yl)-piperidine-1-carboxylic acid[1-(6-benzyloxy-pyridin-3-ylmethyl)-2-[1,4']bipiperidinyl-1'-yl-2-oxo-ethyl]-amide

Product 1

HCID 24863325(+/-)-4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid [2-[1,4']bipiperidinyl-1'-yl-2-oxo-1-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask was charged with 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid[1-(6-benzyloxy-pyridin-3-ylmethyl)-2-[1,4′]bipiperidinyl-1′-yl-2-oxo-ethyl]-amide (27 mg, 0.04 mmol), palladium on charcoal (10%, 4 mg), and methanol (1 mL). The flask was flushed with nitrogen, then hydrogen, and allowed to stir under an atmosphere of hydrogen overnight. The flask was flushed with nitrogen, and the reaction filtered through celite to give 22.1 mg (94%). LC/MS: tR=0.93 min, 590.32 (MH)+.

Workup

  1. customThe flask was flushed with nitrogen
  2. customThe flask was flushed with nitrogen
  3. filtrationthe reaction filtered through celite
  4. customto give 22.1 mg (94%)

Sources & evidence

ORD record
ord-b984319c75be484bae0b1c10cf524163
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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