HCID 10052472, compound → HCID 395456, compound

HRID 366822Notes

Reaction equation

HRID 366822 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=2[N:5]([C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=3[O:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[O:20])[CH2:4]1>C1COCC1.O=[Pt]=O>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:19]([C:21]3[NH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=4[O:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[O:20])[C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 10052472HCID 10052472, compound

Product 1

HCID 395456HCID 395456, compoundYield 123.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14g (120 mg, 0.23 mmol) in THF (45 mL) was hydrogenated over PtO2 (30 mg) at 55 psi for 1.5 h. After removal of the catalyst the solution was concentrated to a small volume under reduced pressure below 30° C., and then diluted with petroleum ether to give 15g (140 mg. 92%), mp 109-111 (C. 1H NMR [(CD3)2SO] δ 11.41 (s, 1 H, NH), 8.07 (d, J=8.8 Hz, 1 H, H-6), 7.75 (d, J=8.2 Hz, 1 H, H-9), 7.64 (s, 1 H, H-4), 7.45 (t, J=7.5 Hz, 1 H, H-8), 7.28 (t, J=7.6 Hz, 1 H, H-7), 7.00 (d, J=1.2 Hz, 1 H, H-3'), 6.73 (d, J=1.9 Hz, 1 H, H-4' or 6'), 6.48 (d, J=2.0 Hz, 1 H, H-4'or 6'), 5.98, 5.96 (2×s, 2 H, NH2), 4.66 (dd, J=10.7, 9.0 Hz, 1 H, H-2), 4.41 (dd, J=11.0, 1.4 Hz, 1 H, H-2), 4.19 (t, J=5.7 Hz, 2 H, OCH2), 4.12-4.04 (m, 1 H, H-1), 3.96 (dd, J=10.9, 3.0 Hz, 1 H, CHHCl), 3.77 (s, 3 H, OCH3), 3.72 (dd, J=11.0, 8.2 Hz, 1 H, CHHCl), 2.73 (t, J=5.7 Hz, 2 H, OCH2CH2), 2.28 (s, 6 H, N(CH3)2).

Workup

  1. customAfter removal of the catalyst the solution
  2. concentrationwas concentrated to a small volume under reduced pressure below 30° C.
  3. additiondiluted with petroleum ether

Sources & evidence

ORD record
ord-d2bfe6002cce441d886f8fef69bdf6cc
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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