HCID 68209985, compound → ethyl 3-[3-methyl-1-(1-methylethyl)-4-({[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-indol-6-yl]propanoate

HRID 873390Notes

Reaction equation

HRID 873390 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:8][C:9]=2[C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:25])[NH:17][C:18]([CH3:24])=[CH:19][C:20]=2[CH2:21][CH2:22][CH3:23])=[O:12])[N:4]([CH:33]([CH3:35])[CH3:34])[CH:3]=1>C(O)C>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:8][C:9]=2[C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:25])[NH:17][C:18]([CH3:24])=[CH:19][C:20]=2[CH2:21][CH2:22][CH3:23])=[O:12])[N:4]([CH:33]([CH3:35])[CH3:34])[CH:3]=1

Participants

3

Reactant 1

HCID 68209985HCID 68209985, compound

Product 1

HCID 67468412ethyl 3-[3-methyl-1-(1-methylethyl)-4-({[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-indol-6-yl]propanoateYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 ml flask was added ethyl (2E)-3-[3-methyl-1-(1-methylethyl)-4-({[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-indol-6-yl]-2-propenoate (120 mg, 0.251 mmol), and Ethanol (10 mL). PdOH2 (70.6 mg, 0.503 mmol) was added and the reaction was degassed with N2 for 15 min then H2 was bubbled in (via balloon) and the reaction stirred for 12 hr. The reaction was purged with N2 for 30 min and then filtered through an acro disc and evaporated. The residue was suspended in MeOH/Water (2 mL/4 mL) and filtered and washed with water to give a white solid. ethyl 3-[3-methyl-1-(1-methylethyl)-4-({[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-indol-6-yl]propanoate (70 mg, 0.146 mmol, 58.1% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.49 (br. s., 1 H) 7.90 (br. s., 1 H) 7.34 (s, 1 H) 7.21 (s, 1 H) 6.82 (s, 1 H) 5.90 (s, 1 H) 4.63-4.73 (m, 1 H) 4.34 (d, J=4.55 Hz, 2 H) 4.04 (q, J=7.07 Hz, 2 H) 2.92 (t, J=7.33 Hz, 2 H) 2.64 (t, J=7.45 Hz, 2 H) 2.55-2.62 (m, 2 H) 2.12 (s, 6 H) 1.52-1.62 (m, 2 H) 1.40 (d, J=6.32 Hz, 6 H) 1.16 (t, J=7.07 Hz, 3 H) 0.94 (t, J=7.20 Hz, 3 H). MS(ES) [M+H]+ 479.8.

Workup

  1. customthe reaction was degassed with N2 for 15 min
  2. customH2 was bubbled in (via balloon)
  3. customThe reaction was purged with N2 for 30 min
  4. filtrationfiltered through an acro disc
  5. customevaporated
  6. filtrationfiltered
  7. washwashed with water
  8. customto give a white solid

Sources & evidence

ORD record
ord-ab989d79e6c040beb190166481508322
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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