Acetic Acid → HCID 52943768, compound

HRID 1162770Notes

Reaction equation

HRID 1162770 reaction equation
[CH2:1]([NH2:3])[CH3:2].[C:4]([C:8]1[C:12]([CH:13]=O)=[CH:11][N:10]([CH2:15][C:16]([NH:18][C:19]2[S:23][C:22]3[CH2:24][CH2:25][CH2:26][CH2:27][C:21]=3[C:20]=2[C:28]([NH2:30])=[O:29])=[O:17])[N:9]=1)([CH3:7])([CH3:6])[CH3:5].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.O>[C:4]([C:8]1[C:12]([CH2:13][NH:3][CH2:1][CH3:2])=[CH:11][N:10]([CH2:15][C:16]([NH:18][C:19]2[S:23][C:22]3[CH2:24][CH2:25][CH2:26][CH2:27][C:21]=3[C:20]=2[C:28]([NH2:30])=[O:29])=[O:17])[N:9]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59520484HCID 59520484, compound

Product 1

HCID 52943768HCID 52943768, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethylamine (175 mg, 0.205 mL, 3.89 mmol) was added to a solution of 2-(2-(3-tert-butyl-4-formyl-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (151 mg, 0.389 mmol) and acetic acid (0.5 mL) in DMF (2.5 mL). Sodium triacetoxyborohydride (824 mg, 3.89 mmol) was added and the mixture stirred for 17 h. Water (300 μL) was added and the reaction stirred for 30 min. The reaction was filtered and purified by preparative reverse phase HPLC. The clean fractions were passed down an SCX cartridge and the product eluted with 2M NH3 in MeOH. Volatiles were blown down to give 2-(2-(3-tert-butyl-4-((ethylamino)methyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (13 mg, 0.031 mmol, 8%).

Workup

  1. stirringthe reaction stirred for 30 min
  2. filtrationThe reaction was filtered
  3. custompurified by preparative reverse phase HPLC
  4. washthe product eluted with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-2a1e2a73f25f43a7bd95ab84d9dccfb6
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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