2-Aminophenol → [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-hydroxy-3-[(2-hydroxyanilino)-methyl]benzoate

HRID 1497996Notes

Reaction equation

HRID 1497996 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C@@H:16]([O:27][C:28](=[O:38])[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=O)[C:30]=3[OH:37])[CH2:17][C:18]3[C:23]([Cl:24])=[CH:22][N+:21]([O-:25])=[CH:20][C:19]=3[Cl:26])[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[OH:46]>CO>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C@@H:16]([O:27][C:28](=[O:38])[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[OH:46])[C:30]=3[OH:37])[CH2:17][C:18]3[C:23]([Cl:24])=[CH:22][N+:21]([O-:25])=[CH:20][C:19]=3[Cl:26])[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:14])[F:15])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 86720699[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-formyl-2-hydroxy-benzoate

Product 1

HCID 86720718[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-hydroxy-3-[(2-hydroxyanilino)-methyl]benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-formyl-2-hydroxy-benzoate (800 mg, 1.41 mmol), MeOH (5 mL) AcOH (0.5 mL) and 2-aminophenol (184 mg, 1.69 mmol) was stirred at room temperature for 16 hours before adding NaBH3(CN) (444 mg, 7.05 mmol) in one portion. The resulting mixture was stirred at room temperature for 3 h, concentrated in vacuo to a sticky pink oil. The residue was used in the next step without further purification. LCMS (Method 2): [MH+]=661 at 3.68 min.

Workup

  1. concentrationconcentrated in vacuo to a sticky pink oil
  2. customThe residue was used in the next step without further purification
  3. customat 3.68 min.

Sources & evidence

ORD record
ord-9845bfa379a642118343f3082b279475
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

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