(2R)-3-aminopropane-1,2-diol → HCID 44229716, compound

HRID 1969485Notes

Reaction equation

HRID 1969485 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[S:22][CH:23]=2)[N:3]=1.[NH2:31][CH2:32][C@@H:33]([OH:36])[CH2:34][OH:35]>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[S:22][CH:23]=[C:19]([CH2:18][S:17][C:4]3[C:5]([C:15]#[N:16])=[C:6]([C:10]4[S:14][CH:13]=[N:12][CH:11]=4)[C:7]([C:8]#[N:9])=[C:2]([NH:31][CH2:32][C@@H:33]([OH:36])[CH2:34][OH:35])[N:3]=3)[N:20]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6994409(2R)-3-aminopropane-1,2-diolHCID 866542122-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

Product 1

HCID 44229716HCID 44229716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg (0.206 mmol) of 2-chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile, together with 38 mg (0.411 mmol) of (2R)-3-aminopropane-1,2-diol, were dissolved in 1.5 ml of THF. The mixture was stirred at room temperature for two hours, and the product was then purified by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added). This gave 64 mg (58%/0 of theory) of the target compound.

Workup

  1. customthe product was then purified by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added)

Sources & evidence

ORD record
ord-a961825a285a4df2bfee533cda953bab
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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