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Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate → Methyl 5-(4-(tert-butoxycarbonylamino)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

HRID 455312
Notes
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Reaction equation

HRID 455312 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:27][NH:28][S:29]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])(=[O:31])=[O:30]>>[C:39]([O:38][C:37]([NH:36][CH2:35][CH2:34][CH2:33][CH2:32][S:29]([N:28]([C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)[CH3:27])(=[O:31])=[O:30])=[O:43])([CH3:42])([CH3:41])[CH3:40]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 11339571Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylateHCID 71699856tert-butyl 4-(N-methylsulfamoyl)butylcarbamate

Product 1

HCID 86667515Methyl 5-(4-(tert-butoxycarbonylamino)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Procedure

The title compound was prepared in a similar fashion as described in Example 2.1, starting from methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 12; 10.3 mmol) and tert-butyl 4-(N-methylsulfamoyl)butylcarbamate (Example 8) to obtain the target compound (3.43 gr).

Sources & evidence

ORD record
ord-15354045f7264a8ca2147ff21759fff4
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497270B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes