Potassium Hydroxide → HCID 178524204, compound

HRID 1525342Notes

Reaction equation

HRID 1525342 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=3)[CH:9]=2)=[CH:6][N:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:3]=1.[OH-].[K+]>CO>[OH:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:22][CH:23]=3)[CH:9]=2)=[CH:6][N:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178468721HCID 178468721, compound

Product 1

HCID 178524204HCID 178524204, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of compound 37-m (300 mg, crude) in MeOH (10 mL) was added a solution of 20% KOH (10 mL). The mixture was stirred at 50° C. for 2 h. The reaction mixture was filtered. The filtrate was concentrated and the aqueous solution was extracted with DCM, and acidified by concentrated HCl to adjust to about pH 2-3. The solid was filtered and washed with water to afford compound 37-1 (110 mg, 73% for two steps) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.827-8.821 (s, 1H), 8.722 (s, 1H), 8.456-8.431 (m, 1H), 8.103-8.035 (m, 2H), 7.733-7.694 (m, 1H), 7.630 (s, 1H), LC-MS (ESI): 361 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. extractionthe aqueous solution was extracted with DCM
  4. filtrationThe solid was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-5c2c52a6fcb048da9e61d00801cb3f59
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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