Dimethylamine → HCID 59186359, compound

HRID 336409Notes

Reaction equation

HRID 336409 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]4[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH3:29][NH:30][CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:29][N:30]([CH2:25][C:24]1[CH:27]=[CH:28][C:21]([NH:20][C:18]2[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=4)[N:16]3[N:17]=2)=[CH:22][CH:23]=1)[CH3:31]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59186516HCID 59186516, compound

Product 1

HCID 59186359HCID 59186359, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

To a solution of 4-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzaldehyde (150 mg, 0.38 mmol) in dichloromethane (50 mL) was added dimethylamine (1 M in THF) (3.6 g, 28 mmol). The resulting mixture was stirred at 24° C. for 1 h. Sodium triacetoxyborohydride was then added to the reaction mixture. After 16 h, the mixture was quenched with saturated aqueous sodium bicarbonate solution. The collected organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative thin layer chromatography afforded the desired product (61 mg, 37% yield). LCMS (ESI) m/z: 421.9.

Workup

  1. waitAfter 16 h
  2. customthe mixture was quenched with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a9fb8ca7e1fb40ec919844a180cdfafd
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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