Acetic Acid → HCID 59520478, compound

HRID 1162769Notes

Reaction equation

HRID 1162769 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([C:9]1[C:13]([CH:14]=O)=[CH:12][N:11]([CH2:16][C:17]([NH:19][C:20]2[S:24][C:23]3[CH2:25][CH2:26][CH2:27][CH2:28][C:22]=3[C:21]=2[C:29]([NH2:31])=[O:30])=[O:18])[N:10]=1)([CH3:8])([CH3:7])[CH3:6].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.O>[C:5]([C:9]1[C:13]([CH2:14][NH:4][CH2:3][CH2:1][OH:2])=[CH:12][N:11]([CH2:16][C:17]([NH:19][C:20]2[S:24][C:23]3[CH2:25][CH2:26][CH2:27][CH2:28][C:22]=3[C:21]=2[C:29]([NH2:31])=[O:30])=[O:18])[N:10]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 59520484HCID 59520484, compound

Product 1

HCID 59520478HCID 59520478, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethanolamine (189 mg, 0.186 mL, 3.09 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 (120 mg, 0.309 mmol) and acetic acid (0.5 mL, 8.7 mmol) in DMF (3 mL) and stirred for 1 h. Sodium triacetoxyborohydride (655 mg, 3.09 mmol) was added and the mixture stirred for 17 h at ambient temperature. Water (500 μL) was added and the mixture stirred for 30 min. The mixture was filtered and purified by preparative reverse phase HPLC. The clean fractions were passed down an SCX cartridge and the free base eluted with 2M NH3 in MeOH. Volatiles were blown down under a nitrogen atmosphere to yield the title compound (54.8 mg, 0.126 mmol, 41%).

Workup

  1. stirringthe mixture stirred for 17 h at ambient temperature
  2. stirringthe mixture stirred for 30 min
  3. filtrationThe mixture was filtered
  4. custompurified by preparative reverse phase HPLC
  5. washthe free base eluted with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-6e0fb91ea5ce4d4485107b65d6145007
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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