Triethylamine → HCID 67238714, compound

HRID 2069140Notes

Reaction equation

HRID 2069140 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25]C.C(Cl)(=O)[O:30]C1C=CC=CC=1.N1CCCC1>C1COCC1>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:25]([N:24]3[CH2:27][CH2:28][CH2:22][CH2:23]3)=[O:30])[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 585325624-(4-Nitronaphthalen-1-yloxy)pyridin-2-amine

Product 1

HCID 67238714HCID 67238714, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (100 mg, 0.356 mmol) and Et3N (100 μL, 0.71 mmol) in dry THF was added phenyl carbonochloridate (49 μL, 0.39 mmol) and the mixture maintained at RT for 2 hr. Pyrrolidine (88 μL, 1.068 mmol) was added and after 16 h at RT the resulting mixture was partitioned between aq NH4Cl (10 mL) and DCM (10 mL). The aq layer was separated and extracted with DCM (3×10 mL) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution) to afford N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)pyrrolidine-1-carboxamide, Intermediate K2, as a yellow solid (110 mg, 79%); Rt 1.84 min (Method 2); m/z 379 (M+H)+ (ES+).

Workup

  1. customwas partitioned between aq NH4Cl (10 mL) and DCM (10 mL)
  2. customThe aq layer was separated
  3. extractionextracted with DCM (3×10 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution)

Sources & evidence

ORD record
ord-b18cac1654fc4e5b80a6968d24eb62f0
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

Loading…