HCID 23206745, compound → HCID 18944985, compound

HRID 399739Notes

Reaction equation

HRID 399739 reaction equation
[CH3:1][C:2]([CH3:38])([P:35](=[O:37])=[O:36])[N:3]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([O:23][CH2:24][CH2:25][NH:26][C:27]2[C:32](Cl)=[CH:31][N:30]=N[C:28]=2Cl)[CH:17]=1)[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH3:15])(=[O:6])=[O:5].[CH3:39]C(C)(P(=O)=O)N(C1C=C(C)C=C(OCCNC2C(Cl)=C(Cl)N=NC=2)C=1)S(C1C=CC=CC=1OCC)(=O)=O>>[CH3:1][C:2]([CH3:38])([P:35](=[O:37])=[O:36])[N:3]([C:16]1[CH:17]=[C:18]([O:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][N:30]=[CH:39][CH:28]=2)[CH:19]=[C:20]([CH3:22])[CH:21]=1)[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH3:15])(=[O:6])=[O:5]

Participants

3

Reactant 2

HCID 23206745HCID 23206745, compoundHCID 23206751HCID 23206751, compound

Product 1

HCID 18944985HCID 18944985, compound

Procedure

was produced in a 54% yield analogously to example 5. Oil. MS (m/e)=518. For this 2-ethoxy-benzenesulfonyl chloride is used in step 5c) instead of 2-methoxy-benzenesulfonyl chloride and one obtained N-(3-cyanomethoxy-5-methyl-phenyl)-2-ethoxy-benzenesulfonamide in a 70% yield (Fp. 142° C.) which was reacted analogously to example 5d) to form N-(dimethyloxophosphinyl-methyl)-N-(3-cyanomethoxy-5-methyl-phenyl)-2-ethoxy-benzene-sulfonamide (46% yield, Fp. 139°-141° C.) and this was reacted analogously to example 5e) to form N-(dimethyloxophosphinyl-methyl)-N-[3-(2-amino-ethoxy)-5-methyl-phenyl]-2-ethoxy-benzenesulfonamide (58% yield, oil, MS (m/e)=440) which was reacted analogously to example 5f) to form a mixture of N-(dimethyloxophosphinylmethyl)-N-{3-[2-(3,5-dichloropyridazin-4-ylamino)-ethoxy]-5-methyl-phenyl}-2-ethoxy-benzenesulfonamide and N-(dimethyloxophosphinyl-methyl)-N-{3-[2-(3,4-dichloropyridazin-5-ylamino)-ethoxy]-5-methyl-phenyl}-2-ethoxy- benzenesulfonamide (55%, Fp. 114°-116° C.) from which the title compound was obtained analogously to example 5g) by catalytic hydrogenation.

Workup

  1. customwas reacted analogously to example 5f)
  2. customto form

Sources & evidence

ORD record
ord-4c9fe456c81b4d6dbce00e9c81401cd0
Source dataset
uspto-grants-1998_10
Patent number
US05824679

Reaction notes

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