Isopropyl isocyanate → HCID 58215732, compound

HRID 1661693Notes

Reaction equation

HRID 1661693 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH3:21])[C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[C:13]([Cl:20])[CH:12]=3)[CH:6]=[N:7][CH:8]=1.[CH:22]([N:25]=[C:26]=[O:27])([CH3:24])[CH3:23]>ClCCl.CO>[Cl:20][C:13]1[CH:12]=[C:11]2[C:16]([C:17]([C:18]#[N:19])=[C:9]([C:5]3[CH:4]=[C:3]([CH2:2][NH:1][C:26]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:27])[CH:8]=[N:7][CH:6]=3)[N:10]2[CH3:21])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 58215751HCID 58215751, compound

Product 1

HCID 58215732HCID 58215732, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-aminomethyl-pyridin-3-yl)-6-chloro-1-methyl-1H-indole-3-carbonitrile (Example 186e, 0.060 g, 0.192 mmol) in dichloromethane (3 mL) is added isopropyl isocyanate (0.027 g, 0.240 mmol) and the reaction is stirred at room temperature for 45 min. The mixture is then washed with water and extracted with dichloromethane twice. The organic phase is concentrated in vacuo to give a residue which is redissolved in methanol. A precipitate crashes out upon standing. The solid is filtered to afford 1-[5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-3-isopropyl-urea as a solid. 1H NMR (400 MHz, MeOD) δ ppm 1.17 (d, J=6.6 Hz, 6H), 3.76-3.91 (m, 4H), 4.52 (s, 2H), 7.38 (dd, J=8.5, 1.9 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H), 8.08 (t, J=2.1 Hz, 1H), 8.73 (d, J=2.0 Hz, 1H), 8.76 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 382.1431 [(M+H)+ Calcd for C20H21N5OCl: 382.1435].

Workup

  1. washThe mixture is then washed with water
  2. extractionextracted with dichloromethane twice
  3. concentrationThe organic phase is concentrated in vacuo
  4. customto give a residue which
  5. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-92fbbc16b773484ba6cf539779e7b9ff
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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