5-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid methyl ester → 5-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid

HRID 222691Notes

Reaction equation

HRID 222691 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][C:12]2[CH:26]=[CH:25][C:15]3[CH2:16][CH2:17][N:18]([CH:21]4[CH2:24][CH2:23][CH2:22]4)[CH2:19][CH2:20][C:14]=3[CH:13]=2)=[CH:7][N:6]=1)=[O:4]>C(O)C.[OH-].[Na+]>[CH:21]1([N:18]2[CH2:19][CH2:20][C:14]3[CH:13]=[C:12]([O:11][C:8]4[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=4)[CH:26]=[CH:25][C:15]=3[CH2:16][CH2:17]2)[CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 104732785-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 103151365-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid methyl ester (E122) (880 mg, 2.5 mmol) was dissolved in a mixture of ethanol (15 ml) and 2N sodium hydroxide (4 ml). The resulting mixture was stirred at room temperature for 0.5 hours and then concentrated in vacuo to remove the organic solvents. The reaction mixture was then acidified to pH 5 (2N hydrochloric acid) and the resulting precipitates were filtered, washed with water and dried under vacuum to afford the title compound (E123a); MS (ES+) m/e 340 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the organic solvents
  3. customthe resulting precipitates
  4. filtrationwere filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-49320cd659e34fe6aa789dd9fad8e679
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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