Hydrochloric Acid → HCID 22477497, compound

HRID 549033Notes

Reaction equation

HRID 549033 reaction equation
C1(C)C=CC(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]2[N:20]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH:21]=[CH:22][CH:23]=2)(=O)=O)=CC=1.ClCCl.Cl>[OH-].[K+]>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=[C:11]1[C:19]1[N:20]([CH2:24][C:25]([OH:27])=[O:26])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 20784602HCID 20784602, compound

Product 1

HCID 22477497HCID 22477497, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A suspension of [2-(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-pyrrol-1-yl]-acetic acid, tert-butyl ester [400 mg, Reference Example 76] in methanolic potassium hydroxide solution (15.4 mL, 100 mg/mL) was agitated for 19 hours at room temperature then treated with dichloromethane (15 mL). This mixture was titrated with aqueous hydrochloric acid (1N) to adjust the pH to 2, then decanted. The organic phase was separated and the aqueous phase was extracted with dichloromethane (10 mL). The combined organic phases were washed with water (15 mL) and then evaporated yielding the title compound (137 mg). LC-MS: METHOD C: RT=2.20 minutes, 242.1[M+H]+ and 198.1 (decarboxylated fragment).

Workup

  1. customdecanted
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with dichloromethane (10 mL)
  4. washThe combined organic phases were washed with water (15 mL)
  5. customevaporated

Sources & evidence

ORD record
ord-4514360986dc410290b961c8d80816d0
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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