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Acetic Acid → (R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944957
Notes
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Reaction equation

HRID 1944957 reaction equation
C(O)(=O)C.[NH2:5][CH2:6][C@@H:7]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([NH:36][C:37]2[C:46]3[C:41](=[C:42]([CH3:68])[CH:43]=[C:44]([S:47]([C:50]4[CH:55]=[CH:54][CH:53]=[C:52]([C:56](=[O:67])[NH:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH:65]=O)[CH:51]=4)(=[O:49])=[O:48])[CH:45]=3)[N:40]=[CH:39][C:38]=2[C:69]([NH2:71])=[O:70])[CH:33]=[CH:34][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:9]([O:8][C@H:7]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[CH2:6][NH:5][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][NH:57][C:56]([C:52]1[CH:51]=[C:50]([S:47]([C:44]2[CH:45]=[C:46]3[C:41](=[C:42]([CH3:68])[CH:43]=2)[N:40]=[CH:39][C:38]([C:69]([NH2:71])=[O:70])=[C:37]3[NH:36][C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([O:29][CH3:28])[CH:31]=2)(=[O:48])=[O:49])[CH:55]=[CH:54][CH:53]=1)=[O:67])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneHCID 866590914-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[(8-oxooctyl)carbamoyl]phenyl]sulfonyl]quinoline-3-carboxamide

Product 1

HCID 86659116
(R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide
Yield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Glacial acetic acid (0.005 mL, 0.089 mmol) and Intermediate 2 (50 mg, 0.149 mmol) were added to a stirring solution of Intermediate 112 (55 mg, 0.089 mmol) in DMF (2 mL) at rt. The resulting solution was stirred for 3 h, then NaBH(OAc)3 (57 mg, 0.267 mmol) was added in portions. The reaction mixture was stirred over night then poured into said. NaHCO3 (40 mL). The precipitate was filtered, washed with H2O (50 mL), and dried to give the title compound (76 mg) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C50H63N6O8SSi+ 935.4. Found m/z=935.4 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred over night
  2. additionthen poured
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O (50 mL)
  5. customdried

Sources & evidence

ORD record
ord-3e5ac4b8714b44548e7e920a2c60aea9
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394829B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes