Cysteamine → 4-Hydroxy-6-methyl-3-[2-(2,3,4-trimethoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepin-4-yl]-5,6-dihydro-pyran-2-one

HRID 982868Notes

Reaction equation

HRID 982868 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[C:14]=1[O:23][CH3:24].OC1C=C(C)OC(=O)C=1C(=O)/C=C/C1C=CC(SC)=CC=1OC.[NH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[SH:56].NCCS>>[OH:1][C:2]1[CH2:7][CH:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10]1[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[C:14]=2[O:23][CH3:24])[S:56][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2[N:49]=1

Participants

5

Reactant 4

HCID 6058CysteamineHCID 87132-AminothiophenolHCID 1356218924-Hydroxy-3-[(E)-3-(2-methoxy-4-methylsulfanyl-phenyl)-acryloyl]-6-methyl-pyran-2-oneHCID 178490174HCID 178490174, compound

Product 1

HCID 1354500444-Hydroxy-6-methyl-3-[2-(2,3,4-trimethoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepin-4-yl]-5,6-dihydro-pyran-2-one

Procedure

Proceeding as in Example 2, but 4-hydroxy-6-methyl-3-[(E)-3-(2,3,4-trimethoxy-phenyl)-acryloyl]-5,6-dihydro-pyran-2-one substituted for 4-hydroxy-3-[(E)-3-(2-methoxy-4-methylsulfanyl-phenyl)-acryloyl]-6-methyl-pyran-2-one and 2-amino-benzenethiol for 2-aminoethanethiol, provided 4-hydroxy-6-methyl-3-[2-(2,3,4-trimethoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepin-4-yl]-5,6-dihydro-pyran-2-one (Compound 56); MS M+ 456.2.

Sources & evidence

ORD record
ord-7bbf327077f141caa227e3fe0ff49324
Source dataset
uspto-grants-2005_03
Patent number
US06861419B2

Reaction notes

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