Triethylamine → Tert-butyl 3-(6-chloro-4-iodopyridin-2-ylamino)cyclohexylcarbamate

HRID 2089057

Reaction equation

HRID 2089057 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH2:15])[CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1.C(N(CC)CC)C.[O:24](C(OC(C)(C)C)=O)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:25](=[O:24])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86649873N1-(6-chloro-4-iodopyridin-2-yl)cyclohexane-1,3-diamine

Product 1

HCID 87185034Tert-butyl 3-(6-chloro-4-iodopyridin-2-ylamino)cyclohexylcarbamateYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of Example 260a (2.60 g, 7.39 mmol) and triethylamine (1.340 mL, 9.61 mmol) in tetrahydrofuran (50 mL) was added BOC2O (1.78 g, 8.13 mmol) at 0° C. The ice bath was removed and the reaction was stirred at room temperature for 90 minutes. The reaction was diluted with EtOAc and washed with brine and sat. NaHCO3. The organic layer was dried over MgSO4, filtered, concentrated, and purified on an 80 g column using the ISCO Companion flash system eluting with hexane/EtOAc (8:2 to 6:4) to give 1.78 g of the title compound.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was diluted with EtOAc
  3. washwashed with brine and sat. NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on an 80 g column
  8. washeluting with hexane/EtOAc (8:2 to 6:4)

Sources & evidence

ORD record
ord-42e50410994c467c8e7938d88b5ad25f
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Linked notes

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