RO-4584820 → HCID 58777663, compound

HRID 1435375Notes

Reaction equation

HRID 1435375 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2F)=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[N:3]=1.[CH3:31][O-:32].[Na+]>CO>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[O:32][CH3:31])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:25][CH2:26]2)[N:3]=1

Participants

4

Reactant 2

HCID 6918852RO-4584820HCID 10942334Sodium Methoxide

Product 1

HCID 58777663HCID 58777663, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A solution of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (49.7 mmol, 0.112 mmol, Example 105) in methanol (4 mL) was treated with sodium methoxide (25 wt % in methanol, 0.29 mL, Aldrich) and heated at 130° C. in microwave for 3 hours. The reaction was concentrated and the crude product was purified on silica gel (95:5 methylene chloride/methanol) to give [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(3-fluoro-2,6-dimethoxy-phenyl)-methanone as a white solid. MS (M+H)+, 454.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude product was purified on silica gel (95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-9f665e45f9da4bf18a84f8dc618179fb
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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