Propane, 1-chloro-3-isocyanato- → HCID 86708108, compound

HRID 1497797Notes

Reaction equation

HRID 1497797 reaction equation
[NH2:1][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.[Cl:35][CH2:36][CH2:37][CH2:38][N:39]=[C:40]=[O:41]>C1COCC1>[Cl:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]([NH:1][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1)=[O:41]

Participants

4

Reactant 2

HCID 166752Propane, 1-chloro-3-isocyanato-HCID 730509764-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

Product 1

HCID 86708108HCID 86708108, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{5-[2-amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 1, 100 mg, 0.218 mmol) and 3-chloropropyl isocyanate (111 μL, 1.089 mmol) in THF (2.5 mL) was heated at 120° C. for 3 hr using microwave irradiation. The reaction mixture was concentrated in vacuo then subjected to flash chromatography eluting with a gradient of 25-100% EtOAc in cyclohexane to give the title compound (125 mg).

Workup

  1. custommicrowave irradiation
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washeluting with a gradient of 25-100% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-f2a41ab71f784457bdb4c09e130c289d
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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