HCID 393692, compound → HCID 393693, compound

HRID 366833Notes

Reaction equation

HRID 366833 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH:7]1[C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12]([N+:20]([O-])=O)=[CH:11][C:10]=2[N:9]([C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH3:35])=[C:29]([O:36][CH3:37])[C:28]=3[O:38][CH3:39])=[O:24])[CH2:8]1)(=[O:4])=[O:3]>C1COCC1.O=[Pt]=O>[NH2:20][C:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[C:15]2[CH:7]([CH2:6][O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH2:8][N:9]([C:23]([C:25]3[NH:26][C:27]4[C:32]([CH:33]=3)=[CH:31][C:30]([O:34][CH3:35])=[C:29]([O:36][CH3:37])[C:28]=4[O:38][CH3:39])=[O:24])[C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 393692HCID 393692, compound

Product 1

HCID 393693HCID 393693, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14o (162 mg, 0.29 mmol) in THF (15 mL) was hydrogenated over PtO2 at 55 psi for 2 h. After removal of the catalyst, the solution was concentrated to a small volume under reduced pressure below 25° C. and diluted with iPr2O to give a crude product. This was purified by precipitation from an EtOAc solution with petroleum ether at 20° C. to give 5-amino-1-[(methanesulfonyloxy)methyl]-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole (15o) (116 mg, 76%) as an unstable solid, mp >260° C. 1H NMR [(CD3)2SO] δ 11.41 (d, J=1.6 Hz, 1 H, NH), 8.08 (d, J=8.5 Hz, 1 H, H-6), 7.76 (d, J=8.3 Hz, 1 H, H-9), 7.67 (s, 1 H, H-4), 7.49 (t, J=7.6 Hz, 1 H, H-8), 7.30 (t, J=7.6 Hz, 1 H, H-7), 7.04 (d, J=2.0 Hz, 1 H, H-3'), 6.96 (s, 1 H, H-4'), 6.15 (v br s, 2 H, NH2), 4.66 (dd, J=10.9, 8.5 Hz, 1 H, H-2), 4.47 (dd, J=9.9, 3.4 Hz, 1 H, H-2), 4.41 (d, J=10.9 Hz, 1 , CHHO), 4.17 (t, J=9.2 Hz, 1 H, CHHO), 4.13-4.04 (m, 1 H, H-1), 3.94 (s, 3 H, OCH3), 3.82 (s, 3 H, OCH3), 3.80 (s, 3 H, OCH3), 3.07 (s, 3 H, SO2CH3). Anal. Calculated for C26H27N3O7S: C, 59.4; H, 5.2; N, 8.0. Found: C, 59.3; H, 5.4; N, 8.1%.

Workup

  1. customAfter removal of the catalyst
  2. concentrationthe solution was concentrated to a small volume under reduced pressure below 25° C.
  3. additiondiluted with iPr2O
  4. customto give a crude product
  5. customThis was purified by precipitation from an EtOAc solution with petroleum ether at 20° C.

Sources & evidence

ORD record
ord-1cf6b3caef894fee9385870375057927
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

Loading…