Ammonium Chloride → HCID 22480268, compound

HRID 1349602Notes

Reaction equation

HRID 1349602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=4)=[O:19])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+:30]>[OH-].[NH4+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4[CH:21]=[CH:22][C:23]([C:24]([NH2:30])=[O:25])=[CH:27][CH:28]=4)=[O:19])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 22479855HCID 22479855, compound

Product 1

HCID 22480268HCID 22480268, compoundYield 357.2%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

The product of example 45 (195 mg, 0.500 mmol) in concentrated ammonium hydroxide (5 mL) and ammonium chloride (1.00 mg) was heated in a sealed tube at 100° C. for 4 hours. The resulting precipitate was filtered, dried and purified by chromatography (SiO2, 80% ethyl acetate/hexanes) to provide the title compound (25 mg, 13% yield). 1H NMR (DMSO-d6) δ 13.24 (br s, 1H), 10.42 (s, 1H), 8.53 (s, 1H), 8.12 (s, 1H), 7.97 (m, 6H), 7.74 (d, 1H), 7.55 (m, 2H), 7.37 (t, 2H); ES-MS (m/z) 375 [M+1]+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried
  3. custompurified by chromatography (SiO2, 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1d650bef7d6a4297af71c4b3835bba0a
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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