Acetic Acid → HCID 59332768, compound

HRID 387333Notes

Reaction equation

HRID 387333 reaction equation
[O:1]=[S:2]1(=[O:28])[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[C:12]([C:25]([NH2:27])=[O:26])[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH3:29][NH:30]C.CC(O)=O.[BH3-]C#N.[Na+]>CS(C)=O.CO>[O:28]=[S:2]1(=[O:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:16]3[C:11](=[C:12]([C:25]([NH2:27])=[O:26])[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:30][CH3:29])[CH:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 59332669HCID 59332669, compound

Product 1

HCID 59332768HCID 59332768, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent2×

Procedure

To 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-formylphenyl)-1H-indole-7-carboxamide (0.160 g, 0.404 mmol) in DMSO (1.8 ml) and MeOH (1.8 ml) was added 2M dimethyl amine in methanol (1.0 ml, 2.0 mmol) and HOAc (0.46 ml, 8.1 mmol). The mixture was allowed to stir for 1 hour, and then NaCNBH3 (0.051 g, 0.808 mmol) was added. After 1 hour, the reaction mixture was concentrated and purified via RP-HPLC (0.1% NH4OH in water/acetonitrile). The fractions containing product were combined and concentrated, giving 0.027 g (15%) of the title compound.

Workup

  1. waitAfter 1 hour
  2. concentrationthe reaction mixture was concentrated
  3. custompurified via RP-HPLC (0.1% NH4OH in water/acetonitrile)
  4. additionThe fractions containing product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f0625868bf2433b9445fb259dc982b6
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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