Methanol → HCID 59736909, compound

HRID 252863Notes

Reaction equation

HRID 252863 reaction equation
[N+](C1C=CC(C2SC=CC=2)=CC=1NC(=O)C1C=CC(C2NN=NN=2)=CC=1)([O-])=O.[C:29]([O:32][CH2:33][CH2:34][N:35]1[C:39]2[CH:40]=[CH:41][C:42]([C:44](=[O:60])[NH:45][C:46]3[CH:51]=[C:50]([C:52]4[S:53][CH:54]=[CH:55][CH:56]=4)[CH:49]=[CH:48][C:47]=3[N+:57]([O-])=O)=[CH:43][C:38]=2[N:37]=[C:36]1[CH3:61])(=[O:31])[CH3:30].CO>C(OCC)(=O)C>[C:29]([O:32][CH2:33][CH2:34][N:35]1[C:39]2[CH:40]=[CH:41][C:42]([C:44](=[O:60])[NH:45][C:46]3[CH:51]=[C:50]([C:52]4[S:53][CH:54]=[CH:55][CH:56]=4)[CH:49]=[CH:48][C:47]=3[NH2:57])=[CH:43][C:38]=2[N:37]=[C:36]1[CH3:61])(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 59736895HCID 59736895, compoundHCID 178521762HCID 178521762, compound

Product 1

HCID 59736909HCID 59736909, compoundYield 96%

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 307 and using ethyl acetate as a solvent instead of methanol, the title compound 308 was obtained in 96% yield. 1H NMR: (DMSO) δ (ppm): 9.70 (s, 1H), 8.23 (s, 1H), 7.87 (dd; J=1.0, 8.4 Hz; 1H); 7.62 (d, J=8.4 Hz; 1H), 7.48 (d; J=2.0 Hz; 1H); 7.34 (dd; J=0.8, 4.8 Hz; 1H); 7.28 (dd; J=2.0, 8.0 Hz; 1H); 7.23 (dd; J=0.8, 3.6 Hz; 1H); 7.03 (dd; J=1.2, 4.8 Hz; 1H); 6.81 (d; J=8.0 Hz; 1H); 5.15 (bs, 2H); 4.52 (t; J=4.8 Hz; 2H); 4.35 (t; J=4.8 Hz; 2H); 2.60 (s, 3H); 1.91 (s, 3H). MS: calc: 434.5; found: 435.2 (M+H)

Sources & evidence

ORD record
ord-798b2602b8b34d8a88d7ebe4cbe98c86
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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