Hydrochloric Acid → 2-Hydroxy-3-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-indole-5-carboxylic acid

HRID 2245556Notes

Reaction equation

HRID 2245556 reaction equation
[OH:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][N:12]=1)=[CH:8][C:7]([C:27]#N)=[CH:6][CH:5]=2.[OH-:29].[Na+].Cl.[OH2:32]>>[OH:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)(=[O:19])=[O:18])=[CH:13][N:12]=1)=[CH:8][C:7]([C:27]([OH:32])=[O:29])=[CH:6][CH:5]=2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 1354426742-hydroxy-3-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-indole-5-carbonitrile

Product 1

HCID 1354951752-Hydroxy-3-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-indole-5-carboxylic acidYield 89%

Procedure

To a mixture of 2-hydroxy-3-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-indole-5-carbonitrile (0.10 g, 0.25 mmol) in water (2 mL) was added 1 M aqueous sodium hydroxide solution (1.3 mL, 1.3 mmol) followed by water (1 mL) in a microwave vial. The mixture was subjected to microwave irradiation for 15 min at 140° C. The pH was adjusted to 5 with 2 M HCl. The solid product was collected by filtration, washed with diethyl ether, and dried to afford 0.11 g (89% yield) of the title compound: MS (ESP) m/z 417 (M++1).

Workup

  1. customirradiation for 15 min at 140° C
  2. filtrationThe solid product was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-d7e3a143914e4f968a6d7610afb9e03c
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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