Methanol → HCID 178491581, compound

HRID 252856Notes

Reaction equation

HRID 252856 reaction equation
[N+](C1C=CC(C2SC=CC=2)=CC=1NC(=O)C1C=CC(C2NN=NN=2)=CC=1)([O-])=O.[CH3:29][O:30][C:31]1[CH:53]=[CH:52][C:34]([C:35]([NH:37][C:38]2[CH:43]=[C:42]([C:44]3[NH:45][N:46]=[N:47][CH:48]=3)[CH:41]=[CH:40][C:39]=2[N+:49]([O-])=O)=[O:36])=[CH:33][CH:32]=1.CO>C(OCC)(=O)C>[NH2:49][C:39]1[CH:40]=[CH:41][C:42]([C:44]2[NH:45][N:46]=[N:47][CH:48]=2)=[CH:43][C:38]=1[NH:37][C:35](=[O:36])[C:34]1[CH:52]=[CH:53][C:31]([O:30][CH3:29])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 178491582HCID 178491582, compoundHCID 178521762HCID 178521762, compound

Product 1

HCID 178491581HCID 178491581, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the same procedure as described in Example 48, step 3 (scheme 36) but substituting compound 171 for the compound 272 and using ethyl acetate as a solvent instead of methanol, the title compound 273 was obtained in 25% yield (over two steps). 1H NMR: (400.2 MHz, DMSO) δ (ppm): 9.62 (s, 1H); 8.08 (bs, 2H); 7.97 (d, J=8.5 Hz; 2H); 7.62 (s, 1H); 7.45 (d, J=8.2 Hz; 1H); 7.03 (d, J=8.5 Hz; 2H); 6.82 (d, J=8.2 Hz; 1H); 5.11 (bs, 2H); 3.83 (s, 3H). MS: calc: 309.3; found: 310.1 (M+H)

Sources & evidence

ORD record
ord-7be8912e8e7443b4a471000fb2794f7f
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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