Ethyl isocyanate → HCID 22184637, compound

HRID 1795357Notes

Reaction equation

HRID 1795357 reaction equation
C(S([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]3[O:22][C:23]4[C:28]([C:29](=[O:31])[CH:30]=3)=[CH:27][C:26]([F:32])=[CH:25][C:24]=4[N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=O)=O)C.C(N(CC)CC)C.[CH2:47]([N:49]=[C:50]=[O:51])[CH3:48]>C(Cl)Cl>[CH2:47]([NH:49][C:50]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]3[O:22][C:23]4[C:28]([C:29](=[O:31])[CH:30]=3)=[CH:27][C:26]([F:32])=[CH:25][C:24]=4[N:33]3[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]3)=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:51])[CH3:48]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 9807818HCID 9807818, compound

Product 1

HCID 22184637HCID 22184637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Fluoro-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (4-piperazin-1-phenyl)-amide (Example 71) (150 mg, 0.216 mmol) was placed in a 50 mL flask with 10 mL of CH2Cl2. This suspension was treated with triethylamine (0.1 mL, 0.67 mmol) and ethylisocyanate (0.21 mL, 18.7 mg, 0.26 mmol) and the reaction stirred at room temperature for 18 hours. The reaction was concentrated (1 mm Hg pressure) and the concentrate purified by chromatography on silica eluting with 1% methanol in chloroform, then concentrated (1 mm Hg pressure). Then triturated with either to yield a yellow powder with was dried under high vacuum for 48 h at 50° C. (79 mg) LCMS−AP+537.4, mp=236–238° C.

Workup

  1. concentrationThe reaction was concentrated (1 mm Hg pressure)
  2. customthe concentrate purified by chromatography on silica eluting with 1% methanol in chloroform
  3. concentrationconcentrated (1 mm Hg pressure)
  4. customThen triturated with
  5. customeither to yield a yellow powder
  6. customwith was dried under high vacuum for 48 h at 50° C. (79 mg) LCMS−AP+537.4, mp=236–238° C.

Sources & evidence

ORD record
ord-fdf52e30f10a4ce6966fb2e10ed564d3
Source dataset
uspto-grants-2006_04
Patent number
US07026314B2

Reaction notes

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