trans-2-Phenylcyclopropyl isocyanate → HCID 68993606, compound

HRID 1930054Notes

Reaction equation

HRID 1930054 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH2:14][CH2:15][NH2:16])[N:12]=[CH:11][C:10]=1[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([CH:26]([CH3:28])[CH3:27])=[N:24][N:25]=2)[N:22]=1.[C:29]1([C@@H:35]2[CH2:37][C@H:36]2[N:38]=[C:39]=[O:40])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH2:14][CH2:15][NH:16][C:39]([NH:38][CH:36]2[CH2:37][CH:35]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:40])[N:12]=[CH:11][C:10]=1[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([CH:26]([CH3:28])[CH3:27])=[N:24][N:25]=2)[N:22]=1

Participants

4

Reactant 2

HCID 255285trans-2-Phenylcyclopropyl isocyanateHCID 57929880HCID 57929880, compound

Product 1

HCID 68993606HCID 68993606, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-(5-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)ethanamine (0.075 g, 0.20 mmol) was dissolved in DCM (4 mL) then trans-2-phenylcyclopropyl isocyanate (0.033 g, 0.21 mmol) was added. The mixture was stirred for about 10 min then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with DCM/MeOH (9:1) as an eluent to give the title compound (0.065 g, 61%): LC/MS (Table 1, Method a) Rt=2.34 min; MS m/z: 543.3 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel with DCM/MeOH (9:1) as an eluent

Sources & evidence

ORD record
ord-eca8a4d0770c4ecebf8122b8efe43490
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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