Isopropyl isocyanate → HCID 57557268, compound

HRID 81911Notes

Reaction equation

HRID 81911 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]([CH3:29])([CH3:28])[CH2:9][N:10]1[C:22]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:23])[C:13]=2[N:12]=[C:11]1[CH2:24][O:25][CH2:26][CH3:27]>ClCCl>[NH2:23][C:14]1[C:13]2[N:12]=[C:11]([CH2:24][O:25][CH2:26][CH3:27])[N:10]([CH2:9][C:8]([NH:7][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])([CH3:28])[CH3:29])[C:22]=2[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 68933946HCID 68933946, compound

Product 1

HCID 57557268HCID 57557268, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, isopropyl isocyanate (206 μL, 2.10 mmol) was added to a chilled (0° C.) solution of 1-(2-amino-2-methylpropyl)-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (628 mg, 2.00 mmol) in dichloromethane (20 mL). The reaction mixture was allowed to warm slowly to ambient temperature overnight. The resulting precipitate was isolated by filtration and then dried under vacuum at 70° C. to provide 669 mg of 1-[2-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-1,1-dimethylethyl]-3-(1-methylethyl)urea as white powder, mp 172.5-173.5° C. Anal. calcd for C20H29N7O2: % C, 60.13; % H, 7.32; % N, 24.54. Found: % C, 59.88; % H, 7.55; % N, 24.51.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-e412d415b74544eb9766629174442fb5
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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