Benzoyl chloride, 3-chloro- → HCID 178522173, compound

HRID 555909Notes

Reaction equation

HRID 555909 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[C:6]([CH:8]=1)[NH2:7].[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19]>>[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH:7][C:6]1[CH:8]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:9]1[NH:13][N:12]=[N:11][N:10]=1)=[O:19]

Participants

3

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 178507674HCID 178507674, compound

Product 1

HCID 178522173HCID 178522173, compoundYield 13%

Procedure

The title compound was prepared essentially according to the method of Example 4, but using 5-Chloro-2-(1H-tetrazol-5-yl)aniline (1.0 mmol) and 3-chlorobenzoyl chloride. After precipitation, the product was further purified by reverse phase C18 preparative HPLC (water/acetonitrile w/0.1% formic acid, 30%-100% eluant gradient) to yield the desired product (46.0 mg, 13%). 1H NMR (400 MHz, d6-DMSO): δ 13.07 (s, 1H), 8.87 (s, 1H), 8.29 (s, 1H), 8.17 (s, 1H), 7.76 (m, 2H), 7.27 (s, 1H), 6.96 (s, 2H). MS (EI) for C14H9Cl2N5O: 334.2 (M+H).

Workup

  1. customThe title compound was prepared essentially
  2. customAfter precipitation
  3. customthe product was further purified by reverse phase C18 preparative HPLC (water/acetonitrile w/0.1% formic acid, 30%-100% eluant gradient)

Sources & evidence

ORD record
ord-931dd42bdb274fe999f16604ba74f2c9
Source dataset
uspto-grants-2011_11
Patent number
US08053454B2

Reaction notes

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