Chloroform → HCID 57906599, compound

HRID 420503Notes

Reaction equation

HRID 420503 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]=[C:11](N)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)[Cl:26]>>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]=[C:11]([Cl:26])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6212ChloroformHCID 57906537HCID 57906537, compound

Product 1

HCID 57906599HCID 57906599, compoundYield 62%

Procedure

A mixture of [2-amino-5-(2,4-dichloro-phenyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester (1.78 g, 4.82 mmol, prepared according to Example 6, Step 3.2), tBuONO (1.05 mL, 8.0 mmol), and CuCl2 (1.01 g, 7.51 mmol) in CHCl3 (6 mL) was stirred at RT for 3 days with exclusion of light. The reaction mixture was concentrated under vacuum, then the remaining residue was suspended in a 2.0 M aqueous Na2CO3 solution (200 mL) and extracted with AcOEt (2×100 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→4:6) to yield the title compound (1.17 g, 3.0 mmol, 62%) as a colorless solid. MS: 388 [M+1]+; HPLC: AtRet=2.89; TLC: RF 0.36 ([hexane/DCM 1:1]/TBME 95:5).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractionextracted with AcOEt (2×100 mL)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→4:6)

Sources & evidence

ORD record
ord-e0ee37d0c74f4088984a22bc15289a9f
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

Loading…