Acetic Acid → HCID 59332641, compound

HRID 387397Notes

Reaction equation

HRID 387397 reaction equation
[O:1]=[S:2]1(=[O:28])[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[C:17]3[C:12](=[C:13]([C:25]([NH2:27])=[O:26])[CH:14]=[C:15]([C:18]4[CH:22]=[C:21]([CH:23]=O)[S:20][CH:19]=4)[CH:16]=3)[NH:11][CH:10]=2)[CH2:4][CH2:3]1.[NH:29]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>CS(C)=O>[O:28]=[S:2]1(=[O:1])[CH2:3][CH2:4][CH:5]([CH2:8][C:9]2[C:17]3[C:12](=[C:13]([C:25]([NH2:27])=[O:26])[CH:14]=[C:15]([C:18]4[CH:22]=[C:21]([CH2:23][N:29]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)[S:20][CH:19]=4)[CH:16]=3)[NH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8119AzepaneHCID 2724942TriacetoxyborohydrideHCID 59332746HCID 59332746, compound

Product 1

HCID 59332641HCID 59332641, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (30 mg, 0.072 mmol), hexahydro-1H-azepine (71.4 mg, 0.720 mmol, 10 eq), acetic acid (0.4 μL, 0.007 mmol, 0.1 eq) were dissolved in DMSO (2 mL) in a 5 mL A-vial reaction tube. The mixture was stirred in VX-2500 Multi-Tube Vortexer for overnight at room temperature. MP-triacetoxyborohydride (309 mg, 0.72 mmol, 10 eq) was then added and the mixture was stirred again in VX-2500 Multi-Tube Vortexer for overnight at room temperature. The reaction mixture was filtered through a polypropylene cartridge (10 mL tube) on Bohdan Miniblock in a reaction tube and was then concentrated and purified by Gilson HPLC with a water-acetonitrile with 0.1% TFA buffer. The desired product fractions were combined and concentrated in a Glas-Col evaporator, giving 3.8 mg (9.5%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a polypropylene cartridge (10 mL tube) on Bohdan Miniblock in a reaction tube
  2. concentrationwas then concentrated
  3. custompurified by Gilson HPLC with a water-acetonitrile with 0.1% TFA buffer
  4. concentrationconcentrated in a Glas-Col evaporator

Sources & evidence

ORD record
ord-0e2701ff2e544786acf67e723b9efd3b
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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