Dimethylamine → HCID 16037389, compound

HRID 1806268Notes

Reaction equation

HRID 1806268 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:32]([NH2:34])=[O:33])[CH:17]=[C:18]([C:21]4[CH:29]=[C:28]([CH:30]=O)[C:24]5[CH2:25][CH2:26][O:27][C:23]=5[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH3:35][NH:36][CH3:37].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:35][N:36]([CH2:30][C:28]1[C:24]2[CH2:25][CH2:26][O:27][C:23]=2[CH:22]=[C:21]([C:18]2[CH:19]=[C:20]3[C:15](=[C:16]([C:32]([NH2:34])=[O:33])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:9]2[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:11][CH2:10]2)[CH:29]=1)[CH3:37]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 86631027HCID 86631027, compound

Product 1

HCID 16037389HCID 16037389, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-formyl-2,3-dihydro-1-benzofuran-6-yl)-1H-indole-7-carboxamide (20 mg, 0.042 mmol) in methanol (2 mL) was added dimethylamine (3 μL, 0.050 mmol), zinc chloride (3 mg, 0.021 mmol) and sodium cyanoborohydride (4 mg, 0.062 mmol). This mixture was reacted in the microwave at 100° C. for 1 h and then removed all solvent. The residue was washed with EtOAc and water. All solvent was removed and purified by Gilson Preparatory HPLC to give 6.0 mg of the title compound (19.6%).

Workup

  1. customThis mixture was reacted in the microwave at 100° C. for 1 h
  2. customremoved all solvent
  3. washThe residue was washed with EtOAc and water
  4. customAll solvent was removed
  5. custompurified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-612e4282f26245ae92546113bb77cfa6
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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