Sodium Hydroxide → HCID 66769308, compound

HRID 2360502Notes

Reaction equation

HRID 2360502 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([C:20]2[N:21]([CH3:44])[C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:29][N:30]2[CH2:35][CH2:34][N:33]([C:36]([CH:38]3[CH2:42][CH2:41][CH2:40][N:39]3[CH3:43])=[O:37])[CH2:32][CH2:31]2)=[O:19])[C:8]([O:15][CH3:16])=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([C:20]2[N:21]([CH3:44])[C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:29][N:30]2[CH2:31][CH2:32][N:33]([C:36]([CH:38]3[CH2:42][CH2:41][CH2:40][N:39]3[CH3:43])=[O:37])[CH2:34][CH2:35]2)=[O:19])[C:8]([O:15][CH3:16])=[C:9]([CH:14]=1)[C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 66985947HCID 66985947, compound

Product 1

HCID 66769308HCID 66769308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.29 g methyl 5-tert-butyl-2-methoxy-3-({1-methyl-7-[4-(1-methyl-pyrrolidine-2-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carbonyl}-amino)-benzoate are dissolved in 25 ml of tetrahydrofuran, combined with 4 ml of 4 N sodium hydroxide solution and heated for 2 hours to 40° C. Then the mixture is heated for 12 hours to 60° C., then a further 2 ml of 4 N sodium hydroxide solution are added and the mixture is heated for a further 12 hours to 60° C. It is then evaporated down in vacuo, the residue is taken up in water and the pH is adjusted to 5 by the addition of 4 N hydrochloric acid. It is extracted 5 times with dichloromethane/isopropanol 4:1 and the combined organic phases are dried on magnesium sulphate. The solvents are eliminated in vacuo and the product thus obtained is further reacted directly.

Workup

  1. temperatureheated for 2 hours to 40° C
  2. temperatureThen the mixture is heated for 12 hours to 60° C.
  3. temperaturethe mixture is heated for a further 12 hours to 60° C
  4. customIt is then evaporated down in vacuo
  5. additionthe pH is adjusted to 5 by the addition of 4 N hydrochloric acid
  6. extractionIt is extracted 5 times with dichloromethane/isopropanol 4:1
  7. customthe combined organic phases are dried on magnesium sulphate
  8. customthe product thus obtained
  9. customis further reacted directly

Sources & evidence

ORD record
ord-a4b73d554071474aaacfce242f1c4804
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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