Hydrochloric Acid → 4-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-pyridazin-3-ylbenzenesulfonamide

HRID 46268Notes

Reaction equation

HRID 46268 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:9]=2[O:10][C:11]2[C:16]([Cl:17])=[CH:15][C:14]([S:18]([N:21](COC)[C:22]3[N:23]=[N:24][CH:25]=[CH:26][CH:27]=3)(=[O:20])=[O:19])=[C:13]([F:31])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.NC1C=C(C2C=C(Cl)C=CC=2OC2C(Cl)=CC(S(/N=C3/N(COC)N=CC=C/3)(=O)=O)=C(F)C=2)C=CN=1.FC(F)(F)C(O)=O.CO.Cl.O>>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:9]=2[O:10][C:11]2[C:16]([Cl:17])=[CH:15][C:14]([S:18]([NH:21][C:22]3[N:23]=[N:24][CH:25]=[CH:26][CH:27]=3)(=[O:19])=[O:20])=[C:13]([F:31])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 6422Trifluoroacetic acidHCID 59436553HCID 59436553, compoundHCID 59436558HCID 59436558, compound

Product 1

HCID 468419344-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-pyridazin-3-ylbenzenesulfonamide

Procedure

4-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyridazin-3-ylbenzenesulfonamide and 4-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-[(3E)-2-(methoxymethyl)pyridazin-3(2H)-ylidene]benzenesulfonamide, (Preparation 875, 93 mg, 0.17 mmol) in trifluoroacetic acid (1 mL, 10 mmol) was stirred for 24 hours. The reaction mixture was concentrated and the residue was taken in methanol (1 mL, 20 mmol) and 2 M of hydrogen chloride in water (1 mL, 2 mmol). After stirring for two days, the reaction mixture was concentrated and the residue liophilized from acetonitrile-water to give 76 mg of product as a hydrochloride salt.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringAfter stirring for two days
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-078ff6a261534a4dba7933756436afe7
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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