Diisopropylethylamine → HCID 67346958, compound

HRID 1969486Notes

Reaction equation

HRID 1969486 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)[O:22][CH:23]=2)[N:3]=1.Cl.[NH:32]1[CH2:35][CH:34]([OH:36])[CH2:33]1.C(N(C(C)C)C(C)C)C>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[O: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]([N:32]4[CH2:35][CH:34]([OH:36])[CH2:33]4)[N:3]=3)[N:20]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 86657021HCID 86657021, compound

Product 1

HCID 67346958HCID 67346958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 mg (0.170 mmol) of 2-chloro-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile, together with 37 mg (0.340 mmol) of azetidin-3-ol hydrochloride and 44 mg (0.340 mmol) of N-ethyl-N-(1-methylethyl)propan-2-amine, were dissolved in 1 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 40 mg (46% 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-ee38808a037d4d8f80b01849693182e4
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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