Hydrochloric Acid → HCID 6480930, compound

HRID 1713939Notes

Reaction equation

HRID 1713939 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.Cl>C1COCC1>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68434137HCID 68434137, compound

Product 1

HCID 6480930HCID 6480930, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(6-methoxypyridin-3-yl)-1H-indole-6-carboxylate (from Step 1, 1 eq.) was dissolved in a mixture THF:MeOH (0.07 M, 1:1, v/v) then an aqueous solution of LiOH monohydrate (3 eq, 0.21 M) was added. The reaction mixture was heated at 60° C. for 4 h. It was allowed to cool to RT, and then hydrochloric acid was added. The precipitate that formed was collected by filtration and dried in vacuo to give the title compound (90%). 1H NMR (400 MHz; DMSO-d6, 300 K) δ 1.17-1.28 (m, 3H), 1.65-1.86 (m, 7H), 2.45-2.55 (m, 1H), 2.8 (s, 3H), 2.96 (s, 3H), 3.94 (s, 3H), 4.91 (s, 2H), 6.97 (d, J 8.4, 1H), 7.62 (d, J 8.8, 1H), 7.65 (d, J 8.8, 1H), 7.82 (d, J 8.4, 1H), 7.95 (s, 1H), 8.11 (s, 1H), 12.6 (bs, 1H); MS (ES+) m/z 436 (M+H)+.

Workup

  1. temperatureto cool to RT
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-25484a816d6d4c638ea24005e6de6eef
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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