HCID 10326621, compound → HCID 10416025, compound

HRID 858072Notes

Reaction equation

HRID 858072 reaction equation
[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([N:21]([CH3:33])[S:22]([C:25]5[C:26]([CH3:32])=[N:27][N:28]([CH3:31])[C:29]=5Cl)(=[O:24])=[O:23])=[CH:17][CH:16]=4)[NH:10][C:9]=3[C:8](=[O:34])[N:7]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[C:6]2=[O:43])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([N:21]([CH3:33])[S:22]([C:25]5[C:26]([CH3:32])=[N:27][N:28]([CH3:31])[CH:29]=5)(=[O:23])=[O:24])=[CH:17][CH:16]=4)[NH:10][C:9]=3[C:8](=[O:34])[N:7]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[C:6]2=[O:43])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 10326621HCID 10326621, compound

Product 1

HCID 10416025HCID 10416025, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 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 (prepared as described in Example 18, 20 mg, 0.032 mmol) in methanol (20 mL) at 25° C. was treated with 10% Pd/C (100 mg). The reaction mixture was submitted to hydrogenation conditions in a Parr bomb at 48 psi for 2 d. At this time, the reaction mixture was filtered through a pad of celite and washed with 90/10 methylene chloride/methanol solution (75 mL). The filtrated was concentrated in vacuo. The resulting residue was purified by HPLC (20–60% acetonitrile/water) to afford 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 (7.0 mg, 37%) as white solid; (ES)+-HRMS m/e calculated for C29H30FN7O4S (M+Na)+ 614.1956, found 614.1955.

Workup

  1. filtrationAt this time, the reaction mixture was filtered through a pad of celite
  2. washwashed with 90/10 methylene chloride/methanol solution (75 mL)
  3. concentrationThe filtrated was concentrated in vacuo
  4. customThe resulting residue was purified by HPLC (20–60% acetonitrile/water)

Sources & evidence

ORD record
ord-63155094aa344762abf69cd72b449188
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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