Diisopropylethylamine → N-Butyl-N-(2,2-dimethoxyethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

HRID 1255331Notes

Reaction equation

HRID 1255331 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]4[CH:25]=[C:26]([CH:35]=[CH:36][CH:37]=4)[CH2:27][CH2:28][O:29][CH2:30][CH2:31][C:32](O)=[O:33])[CH2:18][CH2:17]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:47][O:48][CH:49]([O:56][CH3:57])[CH2:50][NH:51][CH2:52][CH2:53][CH2:54][CH3:55].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.O>[CH2:52]([N:51]([CH2:50][CH:49]([O:48][CH3:47])[O:56][CH3:57])[C:32](=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27][C:26]1[CH:35]=[CH:36][CH:37]=[C:24]([CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][C:15]3([O:14][CH2:13][CH2:12][N:11]([C:9]([C:7]4[N:8]=[C:4]([CH:1]([CH3:2])[CH3:3])[S:5][CH:6]=4)=[O:10])[CH2:16]3)[CH2:17][CH2:18]2)[CH:25]=1)[CH2:53][CH2:54][CH3:55]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21254099N-(2,2-dimethoxyethyl)butan-1-amineHCID 581684843-(3-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid

Product 1

HCID 58168512N-Butyl-N-(2,2-dimethoxyethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(3-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid [Example 34, step c] (0.50 g), Hunig's base (0.58 mL), and N-(2,2-dimethoxyethyl)butan-1-amine [J. Am. Chem. Soc. 1949, 71(6), 2272] (0.12 g) were dissolved in dichloromethane (10 mL). HATU (0.33 g) was then added and the mixture was stirred at room temperature for 24 hours. The mixture was poured into water and extracted with dichloromethane. The organic extracts were combined and evaporated under reduced pressure to give the subtitled compound. Yield 0.45 g.

Workup

  1. extractionextracted with dichloromethane
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b30ce7ffe5454ad7a8ad2f725ea688b6
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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