Hydrochloric Acid → HCID 42605479, compound

HRID 1712182Notes

Reaction equation

HRID 1712182 reaction equation
C(O[C:6](=O)[NH:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[NH2:16])(C)(C)C.[CH:18]1(C=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Cl:26][C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[O:29][CH2:30][C:31](O)=O.[CH:38]1([N+:44]#[C-:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.Cl.C[OH:48]>O1CCOCC1>[Cl:26][C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[O:29][CH2:30][C:31]1[N:7]([CH:6]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[C:45]([NH:44][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:48])[C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[N:16]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 119692-Chlorophenoxyacetic acidHCID 16275CyclohexanecarboxaldehydeHCID 79129Cyclohexyl isocyanideHCID 66619231tert-Butyl (2-amino-4,5-difluorophenyl)carbamate2×

Product 1

HCID 42605479HCID 42605479, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester (24.42 mg, 0.10 mmol, 1.0 equiv; Intermediate C) in MeOH (1.0 mL) was added cyclohexanecarbaldehyde (16.83 mg, 18.05 μl, 0.15 mmol, 1.5 equiv; [2043-61-0]) and the mixture stirred at rt. After 30 min, (2-chloro-phenoxy)-acetic acid (18.66 mg, 0.10 mmol, 1.0 equiv; [CAS RN 614-61-9]) and cyclohexyl isocyanide (10.92 mg, 12.27 pi, 0.10 mmol, 1.0 equiv; [931-53-3]) were added and stirring continued at rt for 2 h. A solution of 4 M HCl in dioxane (0.2 mL) was added and the reaction mixture stirred at rt overnight. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile I water provided 17.5 mg (34%) of the title compound. MS (ISP): 516.2 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued at rt for 2 h
  3. stirringthe reaction mixture stirred at rt overnight
  4. customRemoval of the solvent mixture
  5. customunder reduced pressure and purification by preparative HPLC on reversed phase
  6. washeluting with a gradient of acetonitrile I water

Sources & evidence

ORD record
ord-cef23f7fe806428fb7397ea46f8a11af
Source dataset
uspto-grants-2010_09
Patent number
US07790904B2

Reaction notes

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