Acetic Acid → HCID 69586257, compound

HRID 723213Notes

Reaction equation

HRID 723213 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:30][CH3:31])=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[C:15]([N+:27]([O-])=O)[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[CH3:32]CO.CC(O)=O>[Fe].C(O)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:30][CH3:31])=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]3[N:19]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[CH:32]=[N:27][C:15]=3[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 69586871HCID 69586871, compound

Product 1

HCID 69586257HCID 69586257, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 284Formic AcidSolvent

Procedure

The procedure in Example 318: part e was followed using 5-methylsulfanyl-4-{3-nitro-4-[(pyridin-2-ylmethyl)-amino]-benzenesulfonyl}-thiophene-2-carboxylic acid methyl ester ((Example 264: step c) 41 mg, 0.08 mmol), iron (110 mg, 2 mmol), and EtOH/aq. AcOH, followed by treatment with formic acid to yield the title compound. 1H-NMR (CD3OD): δ 8.50 (m, 1H), 8.42 (s, 1H), 8.08 (m, 1H), 7.97 (d, 1H, J=2.5 Hz), 7.85 (m, 1H), 7.72 (m, 1H), 7.71 (dt, 1H, J=1.9, 7.7 Hz), 7.57 (m, 1H), 7.29 (m, 1H), 7.22 (d, 1H J=7.8 Hz), 6.95 (d, 1H, J=9.0 Hz), 5.57 (s, 2H), 3.82 (s, 3H), 2.56 (s, 3H).

Sources & evidence

ORD record
ord-407f0547a8a3446181fd9f63335789db
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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