HCID 86608208, compound → (+/-)-trans-3-(1H-indol-3-yl)-4-(1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-pyrrolidine-2,5-dione

HRID 405903Notes

Reaction equation

HRID 405903 reaction equation
C(OC([CH:11]1[NH:23][CH2:22][C:20]2=[C:21]3[C:16](=[C:17]([C@H:24]4[C@H:28]([C:29]5[C:37]6[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=6)[NH:31][CH:30]=5)[C:27](=[O:38])[NH:26][C:25]4=[O:39])[CH:18]=[CH:19]2)[CH:15]=[CH:14][N:13]3[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[NH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([C@H:28]2[C@H:24]([C:17]3[CH:18]=[CH:19][C:20]4[CH2:22][NH:23][CH2:11][CH2:12][N:13]5[C:21]=4[C:16]=3[CH:15]=[CH:14]5)[C:25](=[O:39])[NH:26][C:27]2=[O:38])=[CH:30]1

Participants

5

Reactant 2

HCID 86608208HCID 86608208, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67133223(+/-)-trans-3-(1H-indol-3-yl)-4-(1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-pyrrolidine-2,5-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(±)-Trans-7-[4-(1H-indol-3-yl)-2,5-dioxo-pyrrolidin-3-yl]-3,4-dihydro-1H-[1,4]diazepino[6,7,1-hi]indole-2-carboxylic acid benzyl ester (161 mg, 0.31 mmol) and 10% palladium on carbon (100 mg) in anhydrous methanol (15 ml) were stirred under 1 atmosphere of hydrogen for 16 hours. The catalyst was then filtered through a bed of Celite and the filtrate evaporated to dryness to yield (±)-trans-3-(1H-indol-3-yl)-4-(1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-pyrrolidine-2,5-dione as an off white solid (95 mg). 1H NMR (DMSO-d6) 400 MHz δ: 11.04 (d, 1H, J=1.6 Hz), 7.35-7.42 (m, 4H), 7.24 (dd, 1H, J=2.8 and 5.6 Hz), 7.09 (t, 1H, J=7.2 Hz), 6.89-6.98 (m, 3H), 4.52 (dd, 2H, J=7.2 and 24.8 Hz), 4.11 (s, 2H), 4.07-4.10 (m, 2H), 3.14-3.17 (m, 2H).

Workup

  1. filtrationThe catalyst was then filtered through a bed of Celite
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-fdb448c006584cecab61841817657bd4
Source dataset
uspto-grants-2014_06
Patent number
US08754078B2

Reaction notes

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