Ethanol → HCID 18697937, compound

HRID 2289490Notes

Reaction equation

HRID 2289490 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30]4[CH:31]=[CH:32][C:33]5[O:37][C:36]([CH2:38][CH3:39])=[N:35][C:34]=5[CH:40]=4)[N:24]=3)=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[CH2:41](O)[CH3:42]>[Pd]>[CH2:38]([C:36]1[O:37][C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:25]3[N:24]=[C:23]([C:20]4[CH:21]=[CH:22][C:17]([N:14]5[CH2:13][CH2:12][N:11]([CH2:41][CH3:42])[CH2:16][CH2:15]5)=[N:18][CH:19]=4)[CH:28]=[CH:27][N:26]=3)=[CH:40][C:34]=2[N:35]=1)[CH3:39]

Participants

4

Reactant 2

HCID 702EthanolHCID 18697932HCID 18697932, compound

Product 1

HCID 18697937HCID 18697937, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 4-(2-(4-benzyloxycarbonylpiperazin-1-yl)pyrid-5-yl)-N-(2-ethylbenzoxazol-5-yl)-2-pyrimidineamine (100 mg, 0.19 mmol) and 10% palladium on charcoal (30 mg) in ethanol (25 ml) was stirred under an atmosphere of hydrogen at 50° for 2 h, then filtered through Celite® and evaporated. The residue was subjected to column chromatography (silica, 0.88 ammonia solution-methanol-dichloromethane, 1:5:94) to afford the title compound (25 mg) as a white solid m.p. 174-176°. δH (CDCl3) 1.15 (3H, t, J 7.2 Hz), 1.45 (3H, t, J 7.6 Hz), 2.49 (2H, q, J 7.2 Hz), 2.58 (4H, m), 2.96 (2H, q, J 7.6 Hz), 3.71 (4H, m), 6.71 (1H, d, J 9.0 Hz), 7.04 (1H, d, J 5.3 Hz), 7.40 (1H, br s), 7.41 (1H, d, J 8.7 Hz), 7.49 (1H, dd, J 2.1, 8.7 Hz), 8.09 (1H, d, J 2.1 Hz), 8.20 (1H, dd, J 2.4, 9.0 Hz), 8.36 (1H, d, J 5.3 Hz) and 8.87 (1H, d, J 2.1 Hz).

Workup

  1. filtrationfiltered through Celite®
  2. customevaporated

Sources & evidence

ORD record
ord-27ba9795a77144c38343fca9211e8263
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

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