HCID 59232202, compound → HCID 59232186, compound

HRID 1091502Notes

Reaction equation

HRID 1091502 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=4)=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH2:11][OH:12])[N:6]2[N:5]=[CH:4][N:3]=1>C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=4)=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH:11]=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 59232202HCID 59232202, compound

Product 1

HCID 59232186HCID 59232186, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Example 105 (14.7 mg, 0.033 mmol) in THF (3 mL) was added 3,3,3-triacetoxy-3-iodophthalide (42.2 mg, 0.10 mmol). The mixture was stirred at rt under nitrogen for 4 d. The solvent was evaporated under reduced pressure. The residue was dissolved in DMF and purified by HPLC using a gradient of 20-90% MeCN in water to yield 6.0 mg (41%) of the title compound. 1H-NMR (DMSO-d6) 10.34 (s, 1H), 9.90 (bs, 1H), 9.75 (bs, 1H), 8.15 (s, 1H), 8.06-7.99 (m, 2H), 7.59 (d, J=8.6, 2H), 7.51 (dd, J=7.0, 1.1, Hz, 1H), 7.46 (d, J=8.5 Hz, 2H), 7.25 (s, 1H); MS [M+H]+=442.1; LCMS RT=3.29 min.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in DMF
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-9ab0e47b4e4e4fa4a61ea329eaa1a20b
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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