HCID 59754790, compound → HCID 16719076, compound

HRID 1713420Notes

Reaction equation

HRID 1713420 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH:15]=[C:10]3[CH:9]=[C:8]2[CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:4][CH:3]=1>CO.C1COCC1.O.O[Li].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH:15]=[C:10]3[CH:9]=[C:8]2[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:35][CH:36]=1

Participants

4

Reactant 1

HCID 59754790HCID 59754790, compound

Product 1

HCID 16719076HCID 16719076, compound

Reagents, catalysts & solvents 2

HCID 168937Lithium hydroxide, monohydrateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-[1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-propionate (90 mg, 0.180 mmol) was dissolved in a mixture of MeOH:THF:H2O (1:1:1, 2 mL) and LiOH.H2O (25 mg) added. The mixture was heated to 60° C. and monitored by LCMS. After complete reaction the solution was partitioned between EtOAc and water and the aqueous layer acidified with solid citric acid to pH˜4, the organic layer separated, washed with water, dried (MgSO4), filtered and evaporated to yield the title acid. LCMS (ESI) M+H 472.

Workup

  1. additionadded
  2. customAfter complete reaction the solution
  3. customwas partitioned between EtOAc and water
  4. customthe organic layer separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield the title acid

Sources & evidence

ORD record
ord-6957b6c5e1944d89b76b0532889d035b
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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