Methyl Isocyanate → HCID 178485816, compound

HRID 1471814Notes

Reaction equation

HRID 1471814 reaction equation
[C:1]1([N:7]2[C:15](=[O:16])[C:14]3[C:9]([C:10]4[C:11](=[CH:17][NH:18][CH:19]=4)[NH:12][CH:13]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH3:29][N:30]=[C:31]=[O:32]>CN(C=O)C>[CH3:29][NH:30][C:31]([N:18]1[CH:19]=[C:10]2[C:11]([NH:12][CH:13]=[C:14]3[C:15](=[O:16])[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]32)=[CH:17]1)=[O:32]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 178515236HCID 178515236, compound

Product 1

HCID 178485816HCID 178485816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One equivalent of pyrrolo-pyridine 12a was dissolved in DMF (0.1 M) under an atmosphere of nitrogen. 3 equivalents of di-iso-propylethylamine was added, followed by 1.5 equivalents of methylisocyanate and stirred overnight. The crude reaction mixture was concentrated to dryness and purification by column chromatography afforded the compound 13a. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.84 (d, J=3.52 Hz, 3H) 7.02-7.18 (m, 1H) 7.30-7.47 (m, 2H) 7.57-7.78 (m, 1H) 7.90-8.04 (m, 1H) 8.05-8.20 (m, 2H) 8.32-8.50 (m, 1H) 8.52-8.68 (m, 1H) 12.28-12.49 (m, 1H)

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated to dryness and purification by column chromatography

Sources & evidence

ORD record
ord-e9b758d3ce8e4db2a2d5f989dbb69e60
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

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