Sodium Hydroxide → HCID 10326621, compound

HRID 858059Notes

Reaction equation

HRID 858059 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:11][CH2:10]2)[C:6](=[O:12])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:4](=[O:21])[C:3]=1[NH:22][C:23](=O)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]([S:33]([C:36]2[C:37]([CH3:43])=[N:38][N:39]([CH3:42])[C:40]=2[Cl:41])(=[O:35])=[O:34])[CH3:32])=[CH:27][CH:26]=1.[OH-].[Na+]>CO>[CH:9]1([CH2:8][N:7]2[C:2]3[N:1]=[C:23]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([N:31]([CH3:32])[S:33]([C:36]5[C:37]([CH3:43])=[N:38][N:39]([CH3:42])[C:40]=5[Cl:41])(=[O:35])=[O:34])=[CH:29][CH:30]=4)[NH:22][C:3]=3[C:4](=[O:21])[N:5]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]2=[O:12])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58762842HCID 58762842, compound

Product 1

HCID 10326621HCID 10326621, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-{4-[(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl)-methyl-amino]-phenyl}-acetamide (0.119 mmol) in methanol (2 mL) was added 10% w/v aqueous sodium hydroxide solution (1 mL) and the mixture heated to 50° C. for 1.5 hrs. The methanol was removed in vacuo and the aqueous residue acidified to pH=4 with 1.0M aqueous hydrochloric acid. The aqueous suspension was extracted with chloroform, the combined chloroform extracts washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. the residue was triturated with acetonitrile to give 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-methyl-amide as a colorless solid (50%); (ES)+-HRMS m/e calculated for C29H29ClFN7O4S (M+Na)+ 648.1566, found 648.1566.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionThe aqueous suspension was extracted with chloroform
  3. washthe combined chloroform extracts washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-b9593533e19849dab69e07bdee9003c6
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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