Alpha-Cyano-4-Hydroxycinnamic Acid → HCID 178469283, compound

HRID 989545Notes

Reaction equation

HRID 989545 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([N:31]2[CH2:36]COCC2)(=[O:30])=[O:29])(=[O:21])=[O:20])[CH:6]=[C:7]([CH:17]=1)[O:8][CH2:9][CH2:10][CH2:11][O:12][NH:13][C:14]([NH2:16])=[NH:15].[CH3:37][C:38]1C=CC(OS(C2C=CC=C(S(C3OCCNC3)(=O)=O)C=2)(=O)=O)=C(C=1)OCCCON.[C:69]([C:71](=[CH:75][C:76]1C=CC(O)=CC=1)[C:72]([OH:74])=[O:73])#N>>[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([N:31]2[CH2:76][CH2:75][CH:71]([C:72]([O:74][CH2:37][CH3:38])=[O:73])[CH2:69][CH2:36]2)(=[O:30])=[O:29])(=[O:21])=[O:20])[CH:6]=[C:7]([CH:17]=1)[O:8][CH2:9][CH2:10][CH2:11][O:12][NH:13][C:14]([NH2:16])=[NH:15]

Participants

4

Reactant 3

HCID 2102Alpha-Cyano-4-Hydroxycinnamic AcidHCID 22722567HCID 22722567, compoundHCID 178429051HCID 178429051, compound

Product 1

HCID 178469283HCID 178469283, compoundYield 95%

Procedure

{3-[5-Methyl-3-(2-morpholinylsulfonylphenylsulfonyloxy)phenoxy]propoxy}guanidine hydrochloride: The title compound was prepared in 95% yield from 3-[5-methyl-[3-(2-morpholinylsulfonyl)phenylsulfonyloxy]phenoxy]propoxyamine, as prepared in the preceding step, in a manner analogous to step f of Example 1. 1H-NMR (300 MHz, DMSO-d6) δ 8.21 (t, J=8.0 Hz, 2H), 8.04 (t, J=7.8 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.71 (br s, 4H), 6.75 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 3.99 (t, J=6.3 Hz, 2H), 3.90 (t, J=6.4 Hz, 2H), 3.62 (t, J=4.7 Hz, 4H), 3.25 (t, J=4.7 Hz, 4H), 2.22 (s, 3H), 2.02 (t, J=6.3 Hz, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C21H28N4O8S2: 529.1 (M+H), 551.1 (M+Na). Found: 528.9, 550.8.

Workup

  1. customas prepared in the preceding step, in a manner analogous to step f of Example 1

Sources & evidence

ORD record
ord-b5b6dc67a09547fc8d5537c7799150a7
Source dataset
uspto-grants-2003_10
Patent number
US06638931B1

Reaction notes

Loading…