3-Aminophenol → HCID 24963583, compound

HRID 1685105Notes

Reaction equation

HRID 1685105 reaction equation
Cl[CH2:2][C:3]1[NH:15][C:14](=[O:16])[CH:13]2[CH:5]([C:6]3[CH2:7][CH2:8][C:9]4[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=4[C:11]=3[S:12]2)[N:4]=1.C(N(C(C)C)CC)(C)C.[NH2:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O>[OH:37][C:33]1[CH:32]=[C:31]([NH:30][CH2:2][C:3]2[NH:15][C:14](=[O:16])[CH:13]3[CH:5]([C:6]4[CH2:7][CH2:8][C:9]5[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=5[C:11]=4[S:12]3)[N:4]=2)[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 81531DiisopropylethylamineHCID 67264987HCID 67264987, compound

Product 1

HCID 24963583HCID 24963583, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 12E (18 mg), diisopropylethylamine and 3-aminophenol (10 mg) in N,N-dimethylformamide (0.5 mL) were heated at 70° C. for 2 hours. The mixture was cooled and purified by HPLC on a C18 column using 0-70% acetonitrile/0.1% trifluoroacetic acid in water to provide 7 mg of the title compound as the trifluoroacetate salt. 1H NMR (DMSO-d6) δ 12.29 (s, 1H), 9.01 (s, 1H), 8.17 (bs, 1H), 7.53 (m, 1H), 7.31-7.38 (m, 3H), 6.86 (t, J=7.9 Hz, 1H), 6.11 (m, 1H), 6.06 (t, J=2.1 Hz, 1H), 6.03 (dd, J=7.9, 2.1 Hz, 1H), 4.22 (s, 2H), 3.01 (m, 2H), 2.94-2.96 (m, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. custompurified by HPLC on a C18 column

Sources & evidence

ORD record
ord-40cc5ea3e9e14e418172d4e96644f4f8
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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