ethyl 3-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxylate → 3-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxamide

HRID 227468Notes

Reaction equation

HRID 227468 reaction equation
BrC1C=C2C(=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(Cl)(=O)=O.ClS(C1C2C(=C([N+]([O-])=O)C=CC=2)N(S(C2C=CC=CC=2)(=O)=O)C=1C(OCC)=O)(=O)=O.ClC1C=C2C(=CC=1)N(S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(N1CCOCC1)(=O)=O.[N:92]1([S:98]([C:101]2[C:109]3[C:104](=[C:105]([N+:110]([O-:112])=[O:111])[CH:106]=[CH:107][CH:108]=3)[NH:103][C:102]=2[C:113]([O:115]CC)=O)(=[O:100])=[O:99])[CH2:97][CH2:96][O:95][CH2:94][CH2:93]1>>[N:92]1([S:98]([C:101]2[C:109]3[C:104](=[C:105]([N+:110]([O-:112])=[O:111])[CH:106]=[CH:107][CH:108]=3)[NH:103][C:102]=2[C:113]([NH2:7])=[O:115])(=[O:100])=[O:99])[CH2:97][CH2:96][O:95][CH2:94][CH2:93]1

Participants

5

Reactant 4

HCID 57445031ethyl 3-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxylateHCID 68444586ethyl 5-chloro-3-(morpholin-4-ylsulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 86592456ethyl 3-(chlorosulfonyl)-7-nitro-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 574450303-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxamide

Procedure

Following the procedures described in Steps B and C of Example 2 and E of Example 1, replacing in Step B of Example 2 ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 3-(chlorosulfonyl)-7-nitro-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and replacing in Step E of Example 1 ethyl 5-chloro-3-(morpholin-4-ylsulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 3-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxylate, the title compound was obtained. HRMS (ES) exact mass calculated for C13H15N4O6S (M+H+): 355.0707. Found 355.0713.

Sources & evidence

ORD record
ord-b09fb84fe2e449f0a75020e325b77aa0
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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