HCID 68953670, compound → HCID 16041651, compound

HRID 1887467Notes

Reaction equation

HRID 1887467 reaction equation
C([O:8][C:9]1[C:10]([O:36][CH3:37])=[CH:11][C:12]2[CH2:21][CH2:20][N:19]3[CH:14]([CH2:15][C:16]4[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[C:22]([O:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:17]=4[CH2:18]3)[C:13]=2[CH:35]=1)C1C=CC=CC=1>[Ni]>[OH:8][C:9]1[C:10]([O:36][CH3:37])=[CH:11][C:12]2[CH2:21][CH2:20][N:19]3[CH:14]([CH2:15][C:16]4[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[C:22]([O:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:17]=4[CH2:18]3)[C:13]=2[CH:35]=1

Participants

3

Reactant 1

HCID 68953670HCID 68953670, compound

Product 1

HCID 16041651HCID 16041651, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A product obtained in Example 20 (0.09 g, 0.17 mmol) was hydrogenated in the present of Raney-Ni. The desired product was obtained following the synthetic procedure described in Example 1, 4 or 7. The crude product was recrystallized with CH2Cl2/hexane to give pink solid (0.044 g, 59.0%). mp 169˜170° C. 1HNMR (CDCl3) δ: 1.39 (3H, t, CH3), 2.59˜2.68 (3H, m, CH2), 3.10˜3.16 (2H, m, CH2), 3.33˜3.56 (3H, m, CH2 and N—CH), 3.82 (3H, s, Ar—OCH3), 3.88 (3H, s, Ar—OCH3), 4.08 (1H, d, CH2), 4.32 (2H, q, CH2), 5.52 (1H, brs, Ar—OH), 6.60 (1H, s, ArH), 6.87 (1H, s, ArH), 6.91 (1H, s, ArH). MS (EI) m/z: 432 (M−1), 344 (base), 183, 176, 91.

Sources & evidence

ORD record
ord-f00f2fcc865b4f929e8ee632ebf7774d
Source dataset
uspto-grants-2013_08
Patent number
US08501762B2

Reaction notes

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