2-Furancarbonyl chloride → HCID 21081967, compound

HRID 970613Notes

Reaction equation

HRID 970613 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]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:15](=[O:28])[C:14]([C:29]#[N:30])=[C:13]2[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[C:15](=[O:28])[C:14]([C:29]#[N:30])=[C:13]2[N:31]1[CH2:36][CH2:35][N:34]([C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 21081966HCID 21081966, compound

Product 1

HCID 21081967HCID 21081967, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Furoyl chloride (148 μL, 1.5 mmol) was added to a stirred solution of Compound 72 (397 mg, 1 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 ethylacetate to yield 212 mg (43%) of white solids. M.P. 253° C. 1H NMR (DMSO-d6): δ 3.69 (m, 4H), 3.96 (m, 4H), 5.45 (s, 2H), 6.66 (m, 1H), 7.08 (d, J=3.6 Hz, 1H), 7.20 (m, 2H), 7.27 (m, 2H), 7.46 (d, J=9.0 Hz, 1H), 7.69 (dd, J=2.4, 9.0 Hz), 7.89 (s, 1H). EIMS m/z 514 (M+23). Anal. (C26H20ClFN4O3) C, H, N.

Workup

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

Sources & evidence

ORD record
ord-bfa1497865d6448887066c0c89055969
Source dataset
uspto-grants-2007_12
Patent number
US07312221B2

Reaction notes

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