HCID 23206747, compound → HCID 23206752, compound

HRID 399738Notes

Reaction equation

HRID 399738 reaction equation
[CH3:1][C:2]([CH3:39])([P:36](=[O:38])=[O:37])[N:3]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([O:24][CH2:25][CH2:26][NH:27][C:28]2[C:33](Cl)=[CH:32][N:31]=N[C:29]=2Cl)[CH:18]=1)[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[CH3:40]P(C)(C(=O)N(C1C=C(C)C=C(OCCNC2C(Cl)=C(Cl)N=NC=2)C=1)S(C1C=CC=CC=1OCCC)(=O)=O)=O>>[CH3:39][C:2]([CH3:1])([P:36](=[O:38])=[O:37])[N:3]([C:17]1[CH:18]=[C:19]([O:24][CH2:25][CH2:26][NH:27][C:28]2[CH:29]=[CH:40][N:31]=[CH:32][CH:33]=2)[CH:20]=[C:21]([CH3:23])[CH:22]=1)[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]

Participants

3

Reactant 2

HCID 23206747HCID 23206747, compoundHCID 86753228HCID 86753228, compound

Product 1

HCID 23206752HCID 23206752, compound

Procedure

was produced analogously to example 5 in a 33% yield. Oil. MS (m/e)=532. For this 2-propyloxy-benzene-sulfonyl chloride was used in step 5c) instead of 2-methoxy-benzenesulfonyl chloride and one obtained N-(3cyanomethoxy-5-methyl-phenyl)-2-propyloxy-benzene-sulfonamide (Fp. 154°-155° C.) in a 57% yield, which was reacted to N-(dimethyloxo-phosphinyl-methyl)-N-(3-cyanomethoxy-5-methyl-phenyl)-2-propyloxy-benzene-sulfonamide (60% yield, Fp. 143°-145° C.) analogously to example 5d), which was reacted analogously to example 5e) to form N-(dimethyloxophosphinyl-methyl)-N-[3-(2-amino-ethoxy)-5-methyl-phenyl]-2-propyloxy-benzene-sulfonamide (86% yield, oil, MS (m/e)=454), which was reacted analogously to example 5f) to form a mixture of N-(dimethyloxophosphinyl-methyl)-N-{3-[2-(3,5-dichloropyridazin-4-ylamino)-ethoxy]-5-methyl-phenyl}-2-propyloxy-benzenesulfonamide and N-(dimethyloxo-phosphinyl-methyl)-N-{3-[2-(3,4-dichloropyridazin-5-ylamino)-ethoxy]-5-methyl-phenyl}-2-propyloxy-benzene-sulfonamide (quant., oil, MS (m/e)=601) from which the title compound was obtained by catalytic hydrogenation analogously to example 5g).

Workup

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

Sources & evidence

ORD record
ord-0bef81ee08ec4a4783b68bbaa2515316
Source dataset
uspto-grants-1998_10
Patent number
US05824679

Reaction notes

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