Methanol → HCID 12042972, compound

HRID 1244292Notes

Reaction equation

HRID 1244292 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[N:16]=[CH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:13])[CH:5]=[CH:4][NH:3]1.[C:29]1(C)C=CC=CC=1.CO.C[Si](C=[N+]=[N-])(C)C>CCCCCC>[CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:10]=2)[N:16]=1.[CH3:29][N:3]1[CH:4]=[CH:5][C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[N:16]=[CH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:13])=[CH:7][C:2]1=[O:1]

Participants

7

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 69589999HCID 69589999, compound

Product 2

HCID 12042972HCID 12042972, compoundHCID 695898762-[[(1,2-dihydro-1-methyl-2-oxopyridin-4-yl)methyl]amino]-N-(isoquinolin-3-yl)-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

130 mg of 2-[[(1,2-dihydro-2-oxopyridin-4-yl)methyl]amino]-N-(isoquinolin-3-yl)benzoic acid amide is introduced into 4 ml of a mixture that consists of toluene:methanol=1:3.5 and mixed with 0.2 ml of a 2-molar solution of trimethylsilyldlazomethane in hexane and stirred for 8 hours at room temperature. After repeated addition of 0.2 ml of trimethylsilyldiazomethane solution and 1 hour of stirring, the batch is evaporated to the dry state and chromatographed on silica gel with methylene chloride:ethanol=97:3 as an eluant. 20 mg of 2-[(−2-methoxypyridin-4-yl)methyl]amino]-N-(isoquinolin-3-yl)benzic acid amide and 10 mg of 2-[[(1,2-dihydro-1-methyl-2-oxopyridin-4-yl)methyl]amino]-N-(isoquinolin-3-yl)-benzoic acid amide are obtained.

Workup

  1. stirringof stirring
  2. customthe batch is evaporated to the dry state
  3. customchromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-aac18dcdaf854400ba7381fbcf111749
Source dataset
uspto-grants-2006_10
Patent number
US07122547B1

Reaction notes

Loading…