Sodium Hydroxide → HCID 71679681, compound

HRID 2168157Notes

Reaction equation

HRID 2168157 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[C:22]([C:33]#[N:34])[CH:21]=3)[CH:12]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[C:33]([C:22]1[CH:21]=[C:20]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]3[CH:12]=[C:11]([C:8]4[CH:7]=[CH:6][C:5]([C:4]([OH:35])=[O:3])=[CH:10][CH:9]=4)[O:19][C:18]=23)[CH:25]=[CH:24][C:23]=1[O:26][CH:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)#[N:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71679354HCID 71679354, compound

Product 1

HCID 71679681HCID 71679681, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-{7-[3-cyano-4-(tetrahydro-pyran-4-yloxy)-phenyl]-furo[3,2-b]pyridin-2-yl}-benzoic acid ethyl ester (1.6 g, 3.42 mmol) in 50 ml ethanol and 1M NaOH (20 mL, 40.0 mmol) is stirred at room temperature for 14 h. Ethanol is removed in vacuum and the mixture acidified with 1M hydrochloric acid. The resulting precipitate is filtered off, washed with water and dried for 16 h; yield: 1.4 g 4-{7-[3-cyano-4-(tetrahydro-pyran-4-yloxy)-phenyl]-furo[3,2-b]pyridin-2-yl}-benzoic acid; HPLC/MS: 2.12 min, [M+H]=441;

Workup

  1. customEthanol is removed in vacuum
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customdried for 16 h
  5. custom2.12 min, [M+H]=441

Sources & evidence

ORD record
ord-e7372e83cb2d4cbd806f1db415b293b6
Source dataset
uspto-grants-2015_06
Patent number
US09045493B2

Reaction notes

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