Ammonia → HCID 10227639, compound

HRID 1278832Notes

Reaction equation

HRID 1278832 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]([C:15]2[C:27]3[C:26]([CH3:28])=[C:25]([CH3:29])[O:24][C:23]=3[CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:12]=[C:11]([CH2:30][CH3:31])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8](O)=[O:9].C(Cl)(=O)C(Cl)=O.C[N:39](C)C=O.N>C(#N)C.C(O)C.O.C(Cl)Cl>[Br:1][C:2]1[CH:14]=[C:13]([C:15]2[C:27]3[C:26]([CH3:28])=[C:25]([CH3:29])[O:24][C:23]=3[CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:12]=[C:11]([CH2:30][CH3:31])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([NH2:39])=[O:9]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10227702HCID 10227702, compound

Product 1

HCID 10227639HCID 10227639, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[2-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenoxy]-butyric acid (60 mg, 0.12 mmol), oxalyl chloride (10.8 μL, 0.12 mmol), N,N-dimethylformamide (2.0 μL), and methylene chloride (1.0 mL) was stirred at room temperature. After 2.5 h a saturated solution of ammonia in acetonitrile (5 mL) was added and the resulting mixture was stirred at room temperature for 2 days. Concentration under reduced pressure gave a residue, which was suspended in 3% ethanol in water (31 mL) and stirred at room temperature for 18 h. The slurry was filtered, washed well with water, and air dried to give the title compound as an off-white solid (52.6 mg, 88%): NMR (DMSO-d6): δ 8.00 (d,-J=8 Hz, 1H), 7.98 (s, 1H), 7.49 (d, J=8 Hz, 1H), 7.45 (d, J=2 Hz, 1H), 7.43 (ddd, J=1, 7, 8 Hz, 1H), 7.35 (ddd overlapping with a br s, J=1, 7, 8 Hz, 2H), 7.25 (d, J=2 Hz, 1H), 6.79 (br s, 1H), 4.01 (dd, J=6, 9 Hz, 1H), 3.96 (dd, J=6, 9 Hz, 1H), 2.75 (d of quartets, J=7, 15 Hz, 1H), 2.71 (d of quartets, J=7, 15 Hz, 1H), 2.38 (s, 3H), 2.35 (t, J=7 Hz, 2H), 2.04 (quintet, J=7 Hz, 2H), 1.56 (s, 3H), 1.19 (t, J=7 Hz, 3H); MS(+ESI): [M+H]+, 1 bromine isotope pattern, 480/482; Anal. Calc. for C26H26BrNO3Y0.4H2O: C, 64.04, H, 5.54, N, 2.87. Found: C, 64.01, H, 5.43, N, 2.89.

Workup

  1. concentrationConcentration under reduced pressure
  2. customgave a residue, which
  3. stirringstirred at room temperature for 18 h
  4. filtrationThe slurry was filtered
  5. washwashed well with water, and air
  6. customdried

Sources & evidence

ORD record
ord-07cab2cd49a448c19da494b000653fc5
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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