Ethyl isocyanate → HCID 68840036, compound

HRID 2112968Notes

Reaction equation

HRID 2112968 reaction equation
[CH3:1][N:2]([CH3:24])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)[CH2:4]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:35]([N:37]=[C:38]=[O:39])[CH3:36]>C1COCC1>[CH3:1][N:2]([CH3:24])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:38]([NH:37][CH2:35][CH3:36])=[O:39])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68836465HCID 68836465, compound

Product 1

HCID 68840036HCID 68840036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(3-dimethylamino-pyrrolidin-1-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.190 g, 0.6 mmol), and NaHMDS (1.4 ml of 1 M solution in THF, 1.4 mmol) in anhydrous THF (100 ml) was stirred at room temperature for 45 minutes. EtNCO (0.5 ml, 6.3 mmol) was added and the resulting reaction mixture was stirred at room temperature overnight. The reaction was quenched with HCl (0.35 ml of 4 M solution in dioxane). Solvent was evaporated and the resultant material was purified by column chromatography on silica gel (1% NEt3, 0-10% MeOH in CH2Cl2 as eluant), followed by trituration in EtOH, to afford the desired compound as a solid. Mp. 248-250° C. MS (APCI+) 395 (M+1).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at room temperature overnight
  3. customThe reaction was quenched with HCl (0.35 ml of 4 M solution in dioxane)
  4. customSolvent was evaporated
  5. customthe resultant material was purified by column chromatography on silica gel (1% NEt3, 0-10% MeOH in CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-a89029beee654409803a8840fa130a98
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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