Ethyl isocyanate → HCID 54671257, compound

HRID 1522587Notes

Reaction equation

HRID 1522587 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[C:16]4[C:17](=[CH:21][N:22]([CH2:24][CH:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[N:23]=4)[N:18]=[CH:19][CH:20]=3)[CH:11]=[CH:10][N:9]=2)[CH:7]=1.C(N(CC)C(C)C)(C)C.[CH2:41]([N:43]=[C:44]=[O:45])[CH3:42]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[C:16]4[C:17](=[CH:21][N:22]([CH2:24][CH:25]5[CH2:30][CH2:29][N:28]([C:44]([NH:43][CH2:41][CH3:42])=[O:45])[CH2:27][CH2:26]5)[N:23]=4)[N:18]=[CH:19][CH:20]=3)[CH:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 54671256HCID 54671256, compound

Product 1

HCID 54671257HCID 54671257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-(5-Chloro-2-fluorophenyl)pyridin-4-yl)-2-(piperidin-4-ylmethyl)-2H-pyrazolo[4,3-b]pyridin-7-amine (20 mg, 0.046 mmol) and N,N-diisopropylethylamine (7.97 μl, 0.046 mmol) were combined in dichloromethane (1.5 mL) followed by ethyl isocyanate (3.62 μl, 0.046 mmol). The reaction was then stirred at room temperature over night. The solvent was then evaporated to give a residue which was partitioned between EtOAc and 1N NaOH. The organic layer was washed with water and then brine, dried over Na2SO4, filtered, concentrated, and evaporated in-vacuo to give the title compound as a light yellow solid. MS [M+H] found 507.0.

Workup

  1. customThe solvent was then evaporated
  2. customto give a residue which
  3. customwas partitioned between EtOAc and 1N NaOH
  4. washThe organic layer was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customevaporated in-vacuo

Sources & evidence

ORD record
ord-77a0c503fd11453a92541dff29e5cb88
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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