Alpha-Cyano-4-Hydroxycinnamic Acid → HCID 178429050, compound

HRID 1581879Notes

Reaction equation

HRID 1581879 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:5]=[C:6]([O:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38][C:39]([O:41]CC)=[O:40])[CH2:34][CH2:33]2)(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:7]=[C:8]([CH:18]=1)[O:9][CH2:10][CH2:11][CH2:12][O:13][NH:14][C:15]([NH2:17])=[NH:16].C(C(=CC1C=CC(O)=CC=1)C(O)=O)#N>>[CH3:3][C:4]1[CH:5]=[C:6]([O:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38][C:39]([OH:41])=[O:40])[CH2:34][CH2:33]2)(=[O:30])=[O:31])(=[O:21])=[O:22])[CH:7]=[C:8]([CH:18]=1)[O:9][CH2:10][CH2:11][CH2:12][O:13][NH:14][C:15]([NH2:17])=[NH:16]

Participants

3

Reactant 2

HCID 2102Alpha-Cyano-4-Hydroxycinnamic AcidHCID 178472633HCID 178472633, compound

Product 1

HCID 178429050HCID 178429050, compoundYield 85%

Procedure

The title compound was prepared in 85% yield from {3-[5-methyl-3-(2-(4-(ethoxycarbonylmethyl)piperazin-1-ylsulfonyl)phenylsulfonyloxy)phenoxy]propoxy}guanidine dihydrochloride, as prepared in step b of Example 58, in a manner analogous to Example 27. 1H-NMR (300 MHz, DMSO-d6) δ 11.12 (s, 1H), 8.27 (d, J=7.9 Hz, 1H), 8.18 (d, J=7.9 Hz, 1H), 8.08 (t, J=7.7 Hz, 1H), 7.94 (t, J=7.7 Hz, 1H), 7.69 (br s, 4H), 6.76 (s, 1H), 6.51 (s, 1H), 6.47 (s, 1H), 3.99 (t, J=6.2 Hz, 2H), 3.90 (t, J=6.3 Hz, 2H), 3.43 (br s, 6H), 3.25 (br s, 4H), 2.22 (s, 3H), 2.02 (pentet, J=6.2 Hz, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C23H31N5O9S2: 586.2 (M+H), 608.1 (M+Na). Found: 586.2, 608.0.

Workup

  1. customas prepared in step b of Example 58, in a manner analogous to Example 27

Sources & evidence

ORD record
ord-a88037620a214256b68569d2b27f4273
Source dataset
uspto-grants-2004_05
Patent number
US06730783B2

Reaction notes

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