2-Furancarbonyl chloride → HCID 21081972, compound

HRID 346633Notes

Reaction equation

HRID 346633 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[C:14]([C:22]#[N:23])=[C:13]2[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[C:14]([C:22]#[N:23])=[C:13]2[N:24]1[CH2:25][CH2:26][N:27]([C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 21081971HCID 21081971, compound

Product 1

HCID 21081972HCID 21081972, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Furoyl chloride (148 μL, 1.5 mmol) was added to a stirred solution of Compound 73 (303 mg, 1.0 mmol) in pyridine (5 mL) under argon at 0° C. The solution was allowed to come to room temperature and further stirred overnight. The solution was poured into ice water and the solids formed were filtered. The solids were washed by excess water, dried, and recrystallized by ethyl acetate to get 271 mg (68%) of white solids. M.P. 228° C. 1H NMR (DMSO-d6): δ 3.56 (s, 3H), 3.64 (m, 4H), 3.94 (m, 4H), 6.65 (m, 1H), 7.08 (d, J=3.4 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H), 7.79 (dd, J=1.9, 9.0 Hz, 1H), 7.86 (m, 2H). EIMS m/z 419 (M+23). Anal. (C20H17ClN4O3) C, H, N.

Workup

  1. customthe solids formed
  2. filtrationwere filtered
  3. washThe solids were washed by excess water
  4. customdried
  5. customrecrystallized by ethyl acetate

Sources & evidence

ORD record
ord-5f1422780bbb4bbcb6942b0691b14beb
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Reaction notes

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