Sulfuric Acid → 2-(4-Amino-3-fluorophenyl)-5-(5-dimethylaminopentylamino)-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736219Notes

Reaction equation

HRID 1736219 reaction equation
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:14]2[C:15](=[O:33])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25]C(=O)C(C)(C)C)=[C:21]([F:32])[CH:20]=3)[O:18][C:13]=2[C:12]([F:34])=[CH:11][C:10]=1[F:35].S(=O)(=O)(O)O>>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[O:18][C:13]3[C:12]([F:34])=[CH:11][C:10]([F:35])=[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:36])[CH3:1])[C:14]=3[C:15](=[O:33])[CH:16]=2)=[CH:20][C:21]=1[F:32]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 194348925-(5-dimethylaminopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one

Product 1

HCID 194349102-(4-Amino-3-fluorophenyl)-5-(5-dimethylaminopentylamino)-6,8-difluoro-4H-1-benzopyran-4-oneYield 84%

Procedure

Substantially the same manner as that in Example 127 (4) was repeated except that 909 mg (1.81 mmol) of the above 5-(5-dimethylaminopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one was used, treatment with 15 mL of concentrated sulfuric acid was carried out and the resulting compound was recrystallized from ethyl acetate/n-hexane, to give 638 mg of Compound 139 (yield: 84%).

Workup

  1. customthe resulting compound was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-f1f82259d8744d77bdf741eb354f3ef6
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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