HCID 67677187, compound → HCID 18944988, compound

HRID 399740Notes

Reaction equation

HRID 399740 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]=[CH:30][C:29]=2Cl)[CH:18]=1)[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH:14]([CH3:16])[CH3:15])(=[O:6])=[O:5].CP(C)(C(=O)N(C1C=C(C)C=C(OCCNC2C(Cl)=C(Cl)C=NC=2)C=1)S(C1C=CC=CC=1OC(C)C)(=O)=O)=O>>[CH3:39][C:2]([CH3:1])([P:36](=[O:37])=[O:38])[N:3]([C:17]1[CH:18]=[C:19]([O:24][CH2:25][CH2:26][NH:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=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][CH:14]([CH3:16])[CH3:15])(=[O:6])=[O:5]

Participants

3

Reactant 2

HCID 67677187HCID 67677187, compoundHCID 86753229HCID 86753229, compound

Product 1

HCID 18944988HCID 18944988, compound

Procedure

was produced in a 35% yield analogously to example 5. Oil. MS (m/e)=532. For this 2-isopropyloxy-benzene-sulfonyl chloride was used in step 5c) instead of 2-methoxy-benzenesulfonyl chloride and N-(3-cyanomethoxy-5-methyl-phenyl)-2-(2-propyloxy)-benzenesulfonamide (Fp. 100°-102° C.) was obtained in a 21% yield which was reacted analogously to example 5d) to form N-(dimethyloxophosphinyl-methyl)-N-(3-cyanomethoxy-5-methyl-phenyl)-2-(2-propyloxy)-benzenesulfonamide (65% Fp. 137°-140° C.) and this was reacted analogously to example 5e) to form N-(dimethyloxophosphinyl-methyl)-N-[3-(2-amino-ethoxy)-5-methyl-phenyl]-2-(2-propyloxy)-benzene sulfonamide (75% 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-dichloro-pyridin-4-ylamino)-ethoxy]-5-methyl-phenyl}-2-(2-propyloxy)-benzenesulfonamide and N-(dimethyloxo-phosphinyl-methyl)-N-{3-[2-(3,4-dichloro-pyridin-5-ylamino)-ethoxy]5-methyl-phenyl}-2-(2-propyloxy)-benzenesulfonamide (quant., oil, MS (m/e)=601) 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-3f7509b6c48042af89de568c3646c7d4
Source dataset
uspto-grants-1998_10
Patent number
US05824679

Reaction notes

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