Acetic Acid → HCID 59332768, compound

HRID 656095Notes

Reaction equation

HRID 656095 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-33597796d8af48cda651c0357e9d68f5
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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