Hydrochloric Acid → (2-{[4-(4-Chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl}-5,7-dimethyl-1H-indol-1-yl)acetic acid

HRID 844446Notes

Reaction equation

HRID 844446 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[N:11]=[C:12]([NH:23][C:24]([C:26]3[N:27]([CH2:37][C:38]([O:40]C)=[O:39])[C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=4[CH3:36])=[O:25])[S:13][C:14]=2[CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:4]([O:42][CH3:43])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl>O.C(O)CCC>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[N:11]=[C:12]([NH:23][C:24]([C:26]3[N:27]([CH2:37][C:38]([OH:40])=[O:39])[C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=4[CH3:36])=[O:25])[S:13][C:14]=2[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[C:4]([O:42][CH3:43])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86594538HCID 86594538, compound

Product 1

HCID 9852833(2-{[4-(4-Chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl}-5,7-dimethyl-1H-indol-1-yl)acetic acidYield 79.3%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4 g of the compound obtained in step A of Example 5a, 2.65 g of K2CO3 in 9.2 ml of water and 16 ml of n-butanol is heated at 90° C. for 12 hours. After cooling to RT, 19.2 ml of 2N HCl are added. The white precipitate formed is washed with 3 times 200 ml of water and then 3 times 200 ml of ethyl ether. 3.1 g of the expected product are obtained: m.p.=241° C.

Workup

  1. temperatureAfter cooling to RT
  2. customThe white precipitate formed
  3. washis washed with 3 times 200 ml of water

Sources & evidence

ORD record
ord-b148f39e00cb466ea6407bb0fec13a2d
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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