HCID 59508073, compound → HCID 46909566, compound

HRID 1958646Notes

Reaction equation

HRID 1958646 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[N:10](C(OC(C)(C)C)=O)[C:11]3[C:16]([C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][C:14]([C:24](=[O:35])[NH:25][CH2:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1>Cl.O1CCOCC1>[O:32]1[CH2:31][CH2:30][N:29]([CH2:28][CH2:27][CH2:26][NH:25][C:24]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9]([C:8]2[C:3](=[O:2])[NH:4][CH:5]=[CH:6][CH:7]=2)=[C:17]3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:35])[CH2:34][CH2:33]1

Participants

4

Reactant 1

HCID 59508073HCID 59508073, compound

Product 1

HCID 46909566HCID 46909566, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 2-(2-methoxypyridin-3-yl)-5-(3-morpholinopropylcarbamoyl)-3-phenyl-1H-indole-1-carboxylate (0.23 mmol) in 4 N HCl in dioxane (10 ml) was shaken at 70° C. overnight. The reaction mixture was concentrated under reduce pressure. The residue was dissolved in dichloromethane (20 ml) and aqueous NaHCO3 (15 ml). The dichloromethane layer was separated, dried using Na2SO4, filtered and concentrated to give a crude product. The crude product was purified by reverse phase HPLC using TFA as a modifier. The desired product was obtained as yellow solid (0.129 g, 78%); 400 MHz 1H NMR (DMSO-d6) δ: 12.137 (s, 1H), 11.79 (s, 1H), 10.78 (bs, 1H), 8.58 (t, J=5.6, 1H), 8.02 (s, 1H), 7.83-7.63 (m, 1H), 7.61-7.26 (m, 8H), 6.15 (t, J=6.7 Hz, 1H), 5.81-5.71 (m, 1H), 4.01-3.61 (m, 5H), 3.61-3.25 (m, 5H), 3.21-2.94 (m, 4H), 2.04-1.87 (m, 2H); LCMS: 456 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  3. customThe dichloromethane layer was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product
  8. customThe crude product was purified by reverse phase

Sources & evidence

ORD record
ord-9f7ae6a553794836a275c1bb80eb98a5
Source dataset
uspto-grants-2013_04
Patent number
US08410144B2

Reaction notes

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