Cyclohexylamine → HCID 59639649, compound

HRID 556614Notes

Reaction equation

HRID 556614 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[C:10]=3[N:11]=[C:12](S(C)(=O)=O)[N:13]=2)=[C:4]([CH3:30])[CH:3]=1.[CH:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[CH:31]1([NH:37][C:12]2[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[CH3:30])[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[C:10]=3[N:11]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 10113314HCID 10113314, compound

Product 1

HCID 59639649HCID 59639649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 59 (200 mg, 0.47 mmol) and cyclohexylamine (100 mg, 1 mmol) were combined in THF (10 mL) and stirred under Ar at 23° for 18 h. The solvents were removed in vacuo, and the residue was flash chromatographed on silica gel eluted with 50-100% CH2Cl2/hexane. Recrystallization from CH2Cl2/hexane gave the title compound as a white-crystalline solid. mp 181-182°, LC MS m/z=447 (MH+) Retention time=2.71 min.

Workup

  1. customThe solvents were removed in vacuo
  2. customchromatographed on silica gel
  3. washeluted with 50-100% CH2Cl2/hexane
  4. customRecrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-ae540472bcb749b0baa79f72ec39871d
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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