HCID 58659356, compound → HCID 58659362, compound

HRID 1993569Notes

Reaction equation

HRID 1993569 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:23]([C:34]([F:37])([F:36])[F:35])[CH:22]=3)=[O:19])=[CH:13][CH:12]=2)[N:7]=[CH:6][N:5]=1)=[N+]=[N-]>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]4)=[C:23]([C:34]([F:37])([F:36])[F:35])[CH:22]=3)=[O:19])=[CH:13][CH:12]=2)[N:7]=[CH:6][N:5]=1

Participants

4

Reactant 1

HCID 58659356HCID 58659356, compound

Product 1

HCID 58659362HCID 58659362, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenation of N-(4-(4-azidopyrimidin-6-yl-oxy)-phenyl)-N′-(3-trifluoromethyl-4-(piperidin-1-ylmethyl)-phenyl)-urea (Example 130; 213 mg, 0.41 mmol) in the presence of 10% Pd/C (40 mg) in 10 ml of THF during 2 h at rt, filtration and concentration of the filtrate affords the title compound: MS: [M+1]+=487; 1H-NMR (DMSO-d6): 9.09 & 8.92 (2s, 2HN), 8.03 & 7.93 (2s, 2H), 7.69 & 7.65 (2m, 2H), 7.47 & 7.03 (2d, 2×2H), 6.79 (s, 2H), 5.6 (s, 1H), 3.46 (s, 2H), 2.31 (m, 4H), 1.49 (m, 4H), 1.40 (m, 2H).

Workup

  1. filtrationfiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-6f4b6b08725c47c6a54de7ea9e8057dd
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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