HCID 58770836, compound → HCID 58770722, compound

HRID 657237Notes

Reaction equation

HRID 657237 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]4[C:38]5[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=5)[N:32]=[CH:31][N:30]=4)[CH2:25][CH2:24]3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([N:23]3[CH2:24][CH2:25][CH:26]([C:29]4[C:38]5[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=5)[N:32]=[CH:31][N:30]=4)[CH2:27][CH2:28]3)=[O:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58770836HCID 58770836, compound

Product 1

HCID 58770722HCID 58770722, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(4-{[4-(6,7-dimethoxy-quinazolin-4-yl)-piperidine-1-carbonyl]-amino}-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (5 mg, 0.009 mmol), as prepared in Example 61, in MeOH (5 mL) was added 10% Pd/C (5 mg). The solution was degassed and was kept stirring under hydrogen atmosphere for 2 h. It was filtered through a pad of celite and the filtrate was evaporated to afford the desired product (3.7 mg, 74% yield). 1H NMR (300 MHz, CD3OD) δ 8.94 (s, 1H), 7.57 (s, 1H), 7.32 (s, 1H), 7.30 (d, J=8.29 Hz, 2H), 7.15 (d, J=8.51 Hz, 2H), 4.35 (m, 2H), 4.20 (m, 2H), 4.06 (s, 3H), 4.03 (s, 3H), 3.91 (m, 1H), 3.21 (m, 2H), 2.85 (br, 2H), 2.67 (m, 1H), 1.93-2.10 (m, 4H), 1.80 (m, 2H), 1.57 (m, 2H), 1.48 (s, 9H). LC-MS (ESI) calcd mass 575.3, found 576.6 (MH+).

Workup

  1. customThe solution was degassed
  2. filtrationIt was filtered through a pad of celite
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-3e8931341c0941d883e4cea3a57936e0
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

Loading…