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

HRID 446425Notes

Reaction equation

HRID 446425 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]([C:28]1[S:29][CH:30]=[C:31]([C:33]([N:35]2[CH2:40][C:39]3([CH2:45][CH2:44][N:43]([CH2:46][CH2:47][C:48]4[CH:61]=[CH:60][C:51]([CH2:52][CH2:53][O:54][CH2:55][CH2:56][C:57](O)=[O:58])=[CH:50][CH:49]=4)[CH2:42][CH2:41]3)[O:38][CH2:37][CH2:36]2)=[O:34])[N:32]=1)([CH3:27])[CH3:26].[CH3:62][O:63][CH:64]([O:73][CH3:74])[CH2:65][NH:66][CH:67]1[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]1.C(N(CC)CC)C>CN(C=O)C>[CH:67]1([N:66]([CH2:65][CH:64]([O:73][CH3:74])[O:63][CH3:62])[C:57](=[O:58])[CH2:56][CH2:55][O:54][CH2:53][CH2:52][C:51]2[CH:60]=[CH:61][C:48]([CH2:47][CH2:46][N:43]3[CH2:42][CH2:41][C:39]4([O:38][CH2:37][CH2:36][N:35]([C:33]([C:31]5[N:32]=[C:28]([CH:25]([CH3:26])[CH3:27])[S:29][CH:30]=5)=[O:34])[CH2:40]4)[CH2:45][CH2:44]3)=[CH:49][CH:50]=2)[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 462387963-(4-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid

Product 1

HCID 58168489N-cyclohexyl-N-(2,2-dimethoxyethyl)-3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

HATU (0.23 g) was added in one portion to an ice cold solution of 3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid [Example 1, step e] (0.3 g) and N-(2,2-dimethoxyethyl)cyclohexanamine [WO 2008075025] (0.087 g) and triethylamine (0.26 mL) in DMF (10 mL). The mixture was stirred at 20° C. for 1 hour before being partitioned between ethyl acetate and brine. The organic layer was washed with brine (×2), dried, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.32 g.

Workup

  1. custombefore being partitioned between ethyl acetate and brine
  2. washThe organic layer was washed with brine (×2)
  3. customdried
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-df97e2dd95814a03acfe0e6acac4156e
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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