Acetic Acid → 2-(2-(3-Tert-butyl-4-((methylamino)methyl)-1H-pyrazol-1-yl)acetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162774Notes

Reaction equation

HRID 1162774 reaction equation
[CH3:1][NH2:2].[C:3]([C:7]1[C:11]([CH:12]=O)=[CH:10][N:9]([CH2:14][C:15]([NH:17][C:18]2[S:22][C:21]3[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=3[C:19]=2[C:27]([NH:29][CH3:30])=[O:28])=[O:16])[N:8]=1)([CH3:6])([CH3:5])[CH3:4].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[C:3]([C:7]1[C:11]([CH2:12][NH:2][CH3:1])=[CH:10][N:9]([CH2:14][C:15]([NH:17][C:18]2[S:22][C:21]3[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=3[C:19]=2[C:27]([NH:29][CH3:30])=[O:28])=[O:16])[N:8]=1)([CH3:4])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 595205172-(2-(3-Tert-butyl-4-formyl-1H-pyrazol-1-yl)acetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

Product 1

HCID 595205012-(2-(3-Tert-butyl-4-((methylamino)methyl)-1H-pyrazol-1-yl)acetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylamine (45.0 mg, 50 μl, 1.449 mmol) was added to a solution of 2-(2-(3-tert-butyl-4-formyl-1H-pyrazol-1-yl)acetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (100 mg, 0.248 mmol) and acetic acid (100 μl, 1.74 mmol) in DMF (1 mL). Sodium triacetoxyborohydride (527 mg, 2.484 mmol) was added and the reaction stirred for 17 h. The reaction was quenched with water (500 μl) and purified by preparative reverse phase HPLC. The clean fractions were passed down an SCX cartridge and eluted with 2M NH3 in MeOH. Volatiles were blown down under a nitrogen atmosphere to yield the title product (33 mg, 0.079 mmol, 32%).

Workup

  1. customThe reaction was quenched with water (500 μl)
  2. custompurified by preparative reverse phase HPLC
  3. washeluted with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-123c9299f3c14dd2b3cc8cc79ccb862e
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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