4-Fluorophenyl isocyanate → HCID 18969254, compound

HRID 399062Notes

Reaction equation

HRID 399062 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C(O)(=O)C(O)=O.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][C:23]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]([CH3:36])[CH3:35])[N:26]=2)=[O:24])[CH2:16][CH2:15]1.[F:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]=[C:45]=[O:46])=[CH:40][CH:39]=1>O1CCCC1>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][C:45]([NH:13][CH:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][NH:22][C:23]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]([CH:34]([CH3:36])[CH3:35])[N:26]=3)=[O:24])[CH2:18][CH2:19]2)=[O:46])=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 86751129N-[2-(4-amino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide dioxalate

Product 1

HCID 18969254HCID 18969254, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

The product from Example 23, as the free base (0.330 g, 1 mmol) was stirred in 8 mL tetrahydrofuran and cooled in an ice bath to 10° C. To the mixture was added dropwise 4-fluorophenyl isocyanate (0.11 mL, 1 mmol) and the resulting mixture was stirred 1.5 h at room temperature and filtered, and the filtrate was evaporated to an oil. Crystallization as the oxalate salt from ethyl acetate/methanol provided 0.147 g colorless crystals. Mp 158° C. Mass spectrum, m+ =466. Anal (C27H33 FN6O6) theory C, 58.27; H, 5.98; N, 15.10; found C, 58.48; H, 6.23; N, 14.94.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to an oil
  3. customCrystallization as the oxalate salt from ethyl acetate/methanol

Sources & evidence

ORD record
ord-ca5dde2bcc81424d8bef7c56a0f52805
Source dataset
uspto-grants-1998_10
Patent number
US05817676

Reaction notes

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