HCID 20755373, compound → HCID 10182126, compound

HRID 22878Notes

Reaction equation

C(OC(=O)C1C=CC(CN2C(=O)C3C=C(C#CCC4C=CC=CC=4)C=CC=3N(C)S2=O)=CC=1)(C)(C)C.C([O:41][C:42](=[O:72])[C:43]1[CH:48]=[CH:47][C:46]([CH2:49][N:50]2[C:55](=[O:56])[NH:54][C:53]3[CH:57]=[CH:58][C:59]([C:61]#[C:62][CH2:63][C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)=[CH:60][C:52]=3[S:51]2(=[O:71])=[O:70])=[CH:45][CH:44]=1)(C)(C)C>>[O:71]=[S:51]1(=[O:70])[C:52]2[CH:60]=[C:59]([C:61]#[C:62][CH2:63][C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[CH:58]=[CH:57][C:53]=2[NH:54][C:55](=[O:56])[N:50]1[CH2:49][C:46]1[CH:45]=[CH:44][C:43]([C:42]([OH:72])=[O:41])=[CH:48][CH:47]=1

Participants

Reactant 2

HCID 20755373HCID 20755373, compound

HCID 207553754-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2lambda4-benzo[1,2,6]thiadiazin-3-ylmethyl]benzoic acid tert-butyl ester

Product 1

HCID 10182126HCID 10182126, compoundYield 839.9%

Procedure

When in the procedure of Example 4, Step (5) 4-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2λ4-benzo[1,2,6]thiadiazin-3-ylmethyl]benzoic acid tert-butyl ester was replaced with 4-[1,1,3-trioxo-7-(3-phenyl-prop-1-ynyl)-3,4-dihydro-1H-1λ6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoic acid tert-butyl ester (0.12 g, 0.24 mmol) to give 0.9 g (84%) of 4-[1,1,3-trioxo-7-(3-phenyl-prop-1-ynyl)-3,4-dihydro-1H-1λ6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoic acid as a white solid. 1H-NMR (CDCl3); 11.00 (s, 1H), 7.85 (d, 2H), 7.74 (s, 1H), 7.43 (d, 1H), 7.35 (d, 2H), 7.16 (m, 6H), 4.94 (s, 2H), and 3.70 (s, 2H). MS: M++1=447.0 Da

Sources & evidence

ORD record: ord-ac8913d951ae4a58bbf3142eb81671f2
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849648B2

Reaction notes

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