Acetic Acid → HCID 59332768, compound

HRID 387332Notes

Reaction equation

HRID 387332 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.Cl.CN.C(O)(=O)C.[C:36]([BH3-])#[N:37].[Na+]>CO.CS(C)=O>[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:37][CH3:36])[CH:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 59332669HCID 59332669, compound

Product 1

HCID 59332768HCID 59332768, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-formylphenyl)-1H-indole-7-carboxamide (0.160 g, 0.404 mmol) was taken up in MeOH (1.802 mL)/DMSO (1.802 mL). Methyl amine HCl (0.136 g, 2.018 mmol) was added followed by acetic acid (0.462 mL, 8.07 mmol). The reaction mixture was allowed to stir at room temperature for 1 hour. Sodium cyanoborohydride (0.051 g, 0.807 mmol) was added and the reaction mixture was allowed to stir for 45 minutes and LCMS then shows conversion to desired product. The reaction mixture was purified through a 500 mg SCX cartridge eluting with MeOH followed by ammonia in methanol. The fractions are concentrated under a stream of nitrogen. The residue was dissolved in DMSO (˜3 mL) and purified via RP-HPLC using an XBridge Prep C18 column with water/acetonitrile (0.1% NH4OH buffer). Obtained 0.023 g (13.85%) of the title compound.

Workup

  1. stirringto stir for 45 minutes

Sources & evidence

ORD record
ord-8969cb5f8525488da1d558bd746ce5d6
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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