Methanol → HCID 59736695, compound

HRID 252862Notes

Reaction equation

HRID 252862 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20](C2NN=NN=2)=[CH:19][CH:18]=1)([O-])=O.[CH3:29]O.[C:31](OCC)(=[O:33])C>>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([CH3:29])=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:18]=[CH:19][C:20]([O:33][CH3:31])=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 178521762HCID 178521762, compound

Product 1

HCID 59736695HCID 59736695, compoundYield 26%

Procedure

Following the same procedure as described in Example 48, step 3 (scheme 36) but substituting compound 171 for compound 94dd and using ethyl acetate as a solvent instead of methanol, the title compound 302 was obtained in 26% yield. 1H NMR: (400.2 MHz, DMSO) δ (ppm): 9.60 (s, 1H), 7.96 (d, J=8.0, Hz, 2H); 7.36 (d, J=2.1 Hz, 1H); 7.20 (dd, J=2.1, 8.3 Hz, 1H); 7.03 (d, J=8.0, Hz, 2H); 7.00 (d, J=3.5 Hz, 1H); 6.78 (d, J=8.3 Hz, 1H), 6.70 (dd, J=1.1, 3.5 Hz, 1H); 3.83 (s, 3H); 2.42 (d, J=1.1 Hz, 3H). MS: calc: 338.4; found: 338.4 (M+H).

Sources & evidence

ORD record
ord-4094f3f0f03842f38d3ae341a042a265
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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