Sodium Methoxide → Rho-Kinase-IN-1

HRID 1911888Notes

Reaction equation

HRID 1911888 reaction equation
CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][CH:23]=4)[CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=O.C[O-].[Na+]>CO>[CH3:29][S:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:17]2[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][C:10]3[CH:9]=[C:8]4[C:13](=[CH:12][CH:11]=3)[NH:5][N:6]=[CH:7]4)[CH2:16]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 597997752,2-Dimethyl-1-(5-(1-(4-(methylthio)benzyl)piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one

Product 1

HCID 25008330Rho-Kinase-IN-1Yield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 25 mL round bottom flask were added 2,2-dimethyl-1-(5-(1-(4-(methylthio)benzyl)piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one (250 mg, 0.6 mmol), methanol (5 mL), and sodium methoxide (93 mg, 1.7 mmol). The reaction was stirred at room temperature until the starting material was consumed as monitored by HPLC. The mixture was diluted with ethyl acetate (10 mL), washed with water (2×10 mL), and the organic phase was separated, dried over MgSO4, filtered and evaporated to dryness to afford the title compound (180 mg, 89%).

Workup

  1. customwas consumed
  2. additionThe mixture was diluted with ethyl acetate (10 mL)
  3. washwashed with water (2×10 mL)
  4. customthe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-30c18dc8230c454cbb5e36cad19ca85c
Source dataset
uspto-grants-2013_12
Patent number
US08604205B2

Reaction notes

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