Water → HCID 86659108, compound

HRID 1944949Notes

Reaction equation

HRID 1944949 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[CH:11][C:10]([S:23]([C:26]1[CH:27]=[C:28]([CH:44]=[CH:45][CH:46]=1)[C:29]([N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38]OS(C)(=O)=O)[CH2:33][CH2:32]1)=[O:30])(=[O:25])=[O:24])=[CH:9][C:8]=2[CH3:47])(=[O:3])[NH2:2].[NH2:48][CH2:49][C@@H:50]([C:59]1[CH:68]=[CH:67][C:66]([OH:69])=[C:65]2[C:60]=1[CH:61]=[CH:62][C:63](=[O:70])[NH:64]2)[O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53].CCN(C(C)C)C(C)C.O>CS(C)=O>[Si:52]([O:51][CH:50]([C:59]1[CH:68]=[CH:67][C:66]([OH:69])=[C:65]2[C:60]=1[CH:61]=[CH:62][C:63](=[O:70])[NH:64]2)[CH2:49][NH:48][CH2:38][CH2:37][N:34]1[CH2:35][CH2:36][N:31]([C:29]([C:28]2[CH:27]=[C:26]([S:23]([C:10]3[CH:11]=[C:12]4[C:7](=[C:8]([CH3:47])[CH:9]=3)[N:6]=[CH:5][C:4]([C:1]([NH2:2])=[O:3])=[C:13]4[NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)(=[O:25])=[O:24])[CH:46]=[CH:45][CH:44]=2)=[O:30])[CH2:32][CH2:33]1)([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneHCID 86659109HCID 86659109, compound

Product 1

HCID 86659108HCID 86659108, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of Intermediate 138 (360 mg, 0.53 mmol) and Intermediate 2 (209 mg, 0.53 mmol) in 3 mL DMSO, DIEA (276 μL, 1.59 mmol) was added at 50° C. The reaction mixture was stirred for 1 h and water was added. The solid was collected by filtration and purified with prep HPLC to give the title compound. ES/MS calcd. for C48H58N7O8Ssi+ 920.4. Found m/z=920.3 (M+H)+.

Workup

  1. filtrationThe solid was collected by filtration
  2. custompurified with prep HPLC

Sources & evidence

ORD record
ord-6ee21ca89df34c6d8b769e2105ffa619
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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