Sodium Hydroxide → HCID 67238228, compound

HRID 1521767Notes

Reaction equation

HRID 1521767 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][N:16]4[C:23]=3[N:24]=2)=[O:9])[N:4]=[C:3]1[C:25]([O:27]CC)=[O:26].[OH-].[Na+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][N:16]4[C:23]=3[N:24]=2)=[O:9])[N:4]=[C:3]1[C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67237114HCID 67237114, compound

Product 1

HCID 67238228HCID 67238228, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of ethyl 1-methyl-4-{[(6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepin-2-yl)carbonyl]amino}-1H-imidazole-2-carboxylate (Example 28, 160 mg, 0.40 mmol) in methanol (3 mL) is added 2M aqueous NaOH (0.4 mL). The mixture is stirred at 60° C. for 3 h and is then cooled to room temperature. The methanol is removed in vacuo and the aqueous mixture is acidified to pH 5 with 1N aqueous HCl. The resulting solid is collected by filtration and dried in vacuo to afford the title compound as a yellow solid (130 mg, 87%). LCMS: 369.20 (M+H+). (System V)

Workup

  1. temperatureis then cooled to room temperature
  2. customThe methanol is removed in vacuo
  3. filtrationThe resulting solid is collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7470dbc3a3e44ece9143de59515de1f1
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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