HCID 59511752, compound → HCID 59511754, compound

HRID 1157475Notes

Reaction equation

HRID 1157475 reaction equation
[CH:1]([NH:4][C:5](=[O:45])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:18](CC3C=CC(OC)=CC=3)[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[N:9]=[C:8]1[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([NH:4][C:5](=[O:45])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:14]=2)[N:9]=[C:8]1[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59511752HCID 59511752, compound

Product 1

HCID 59511754HCID 59511754, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-isopropyl-2-[6-[(4-methoxybenzyl)-(3-piperidin-1-ylpropyl)amino]-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]acetamide (EXAMPLE 3r) (44 mg, 0.07 mmol) in ethanol (7 mL) was added 10% Pd/C (−25 mg, catalytic). The mixture was stirred under an atmosphere of hydrogen (50 p.s.i.) for 18 h. The mixture was filtered through CELITE™ and concentrated in vacuo. The resulting oil was purified by chromatography on a silica gel with methanol:dichloromethane (1:9, v/v) as eluent. The resultant yellow solid was further purified using preparatory HPLC to yield N-isopropyl-2-[2-(3-methoxyphenyl)-4-oxo-6-(3-piperidin-1-ylpropylamino)-4H-quinazolin-3-yl]acetamide (EXAMPLE 13a) (9 mg, 0.02 mmol, 24%) as a yellow solid.

Workup

  1. filtrationThe mixture was filtered through CELITE™
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was purified by chromatography on a silica gel with methanol:dichloromethane (1:9, v/v) as eluent
  4. customThe resultant yellow solid was further purified

Sources & evidence

ORD record
ord-7827e94e505f4cd1b30283d57ab13cb8
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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