HCID 118317161, compound → HCID 118307483, compound

HRID 2283228Notes

Reaction equation

HRID 2283228 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)(=[O:3])[CH3:2]>CCO.[Ni]>[C:1]([NH:4][CH2:5][C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:9]=[CH:10][C:11]=1[NH2:12])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 118317161HCID 118317161, compound

Product 1

HCID 118307483HCID 118307483, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 15 (1.13 g, 3 mmol) in EtOH (30 mL) was added Ra—Ni (0.20 g, 10% wet basis) and the mixture was subjected to hydrogenation in Parr apparatus at 20 psi for 6 hours. After filtering over the pad of celite, the solution was concentrated and purified over silica column, eluting with CH2Cl2:MeOH (95:5) and then changing to (92:8) afforded compound 16 as a light yellow thick oil (0.85 g, 82%). IR (KBr) vmax. cm−1: 3441, 3421 (NH), 3042 (Ar—H), 2960 (Alph-H), 1699, 1696 (C═O), 1607, 1577 (C═C), 1240 (C—N), 1165 (C—O). 1H NMR (500 MHz, CDCl3) δ=1.48 (s, 9H, (C(CH3)3), 2.16 (s, 3H, CH3), 3.38 (br. s, 4H, 2CH2), 3.52 (br. s, 4H, 2CH2), 5.28 (br. s, 2H, NH2), 5.49 (s, 2H, CH2), 6.78 (dd, 1H, J=2.3, 9.3 Hz, H-6), 6.80 (br. s, 1H, H-2), 6.87 (d, 1H, J=9.2 Hz, H-5). 13C NMR (125.7 MHz, CDCl3) δ=20.97 (CH3), 28.35 (C(CH3)3), 42.53 (CH2), 46.26 (CH2), 62.54 (CH2), 79.85 (C(CH3)3), 112.10 (aromatic-C), 112.38 (aromatic-C), 117.09 (aromatic-C), 130.22 (aromatic-C), 135.03 (aromatic-C), 143.02 (aromatic-C), 154.58 (CO), 170.51 (CO). Calculated (%) for C18H28N4O3 (348.22); C, 62.05; H, 8.10; N, 16.08. found (%); C, 62.00; H, 8.15; N, 16.00.

Workup

  1. filtrationAfter filtering over the pad of celite
  2. concentrationthe solution was concentrated
  3. custompurified over silica column
  4. washeluting with CH2Cl2:MeOH (95:5)

Sources & evidence

ORD record
ord-36e0efa02f3c43b4954d2cf25447a830
Source dataset
uspto-grants-2015_09
Patent number
US09145388B2

Reaction notes

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