Ethyl isocyanate → HCID 54674998, compound

HRID 2362732Notes

Reaction equation

HRID 2362732 reaction equation
[Cl:1][C:2]1[C:3]([C:17]2[S:21][C:20]([C:22]3([NH2:26])[CH2:25][CH2:24][CH2:23]3)=[N:19][CH:18]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28]>O1CCCC1.O.[Cl-].[Na+].O>[Cl:1][C:2]1[C:3]([C:17]2[S:21][C:20]([C:22]3([NH:26][C:30]([NH:29][CH2:27][CH3:28])=[O:31])[CH2:25][CH2:24][CH2:23]3)=[N:19][CH:18]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 8022Ethyl isocyanateHCID 54674996HCID 54674996, compound

Product 1

HCID 54674998HCID 54674998, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanamine (30 mg, 0.078 mmol) (Example 121B) in anhydrous tetrahydrofuran (1 mL) was treated with ethyl isocyanate (6.79 μL, 0.086 mmol), and the reaction mixture was stirred at ambient temperature for about 4 hours. The reaction was diluted with water and brine, and extracted with dichloromethane. The extracts were combined and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 2% to 8% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 456.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) ppm 12.34 (s, 1H) 8.26 (s, 1H) 8.22 (s, 1H) 8.16 (s, 1H) 8.03 (s, 1H) 7.06 (s, 1H) 6.75 (s, 1H) 5.93 (t, 1H) 3.89 (s, 3H) 3.01 (dd, 2H) 2.70 (m, 2H) 2.40 (m, 2H) 2.05 (m, 2H) 0.99 (t, 3H).

Workup

  1. extractionextracted with dichloromethane
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel
  4. washeluting with a gradient of 2% to 8% methanol in dichloromethane

Sources & evidence

ORD record
ord-6286f959048b4c00a7d38e82310c367f
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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