(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde → (R)-5-(1-(tert-Butyldimethylsilyloxy)-2-(1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-8-hydroxyquinolin-2(1H)-one

HRID 1689520Notes

Reaction equation

HRID 1689520 reaction equation
[Si:1]([O:8][C@H:9]([C:24]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28](=[O:35])[NH:29]2)[CH2:10][NH:11][C:12]([CH3:23])([CH3:22])[CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:36]([C:39]1[S:43][CH:42]=[C:41]([C:44]([N:46]2[CH2:51][C:50]3([CH2:56][CH2:55][NH:54][CH2:53][CH2:52]3)[O:49][CH2:48][CH2:47]2)=[O:45])[CH:40]=1)([CH3:38])[CH3:37]>>[Si:1]([O:8][C@H:9]([C:24]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28](=[O:35])[NH:29]2)[CH2:10][NH:11][C:12]([CH3:23])([CH3:22])[CH2:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:16]([CH2:17][N:54]2[CH2:53][CH2:52][C:50]3([O:49][CH2:48][CH2:47][N:46]([C:44]([C:41]4[CH:40]=[C:39]([CH:36]([CH3:38])[CH3:37])[S:43][CH:42]=4)=[O:45])[CH2:51]3)[CH2:56][CH2:55]2)[CH:15]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 57989117(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehydeHCID 57989215(5-Isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Product 1

HCID 57989329(R)-5-(1-(tert-Butyldimethylsilyloxy)-2-(1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-8-hydroxyquinolin-2(1H)-one

Procedure

The subtitled compound was prepared using a similar method to that described in Example 14, step b) using (R)-3-(2-(2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde (0.32 g) (Example 275, step h) and (5-isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (0.21 g) (Example 275, step i)). The crude product was purified by flash silica chromatography, 8% methanol in dichloromethane with 1% 880 aqueous ammonia. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.31 g.

Workup

  1. customThe subtitled compound was prepared
  2. customThe crude product was purified by flash silica chromatography, 8% methanol in dichloromethane with 1% 880 aqueous ammonia
  3. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-22a6b90aebaa42928e721393ba23597e
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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