Triethylamine → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanamide

HRID 446485Notes

Reaction equation

HRID 446485 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.FC(F)(F)C(O)=O.[CH:32]([C:35]1[S:36][CH:37]=[C:38]([C:40]([N:42]2[CH2:66][C:46]3([CH2:49][N:48]([CH2:50][CH2:51][C:52]4[CH:53]=[C:54]([CH:63]=[CH:64][CH:65]=4)[CH2:55][CH2:56][O:57][CH2:58][CH2:59][C:60](O)=[O:61])[CH2:47]3)[O:45][CH2:44][CH2:43]2)=[O:41])[N:39]=1)([CH3:34])[CH3:33].[CH3:67][O:68][CH:69]([O:78][CH3:79])[CH2:70][NH:71][CH:72]1[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]1.C(N(CC)CC)C>CN(C=O)C>[CH:72]1([N:71]([CH2:70][CH:69]([O:78][CH3:79])[O:68][CH3:67])[C:60](=[O:61])[CH2:59][CH2:58][O:57][CH2:56][CH2:55][C:54]2[CH:63]=[CH:64][CH:65]=[C:52]([CH2:51][CH2:50][N:48]3[CH2:47][C:46]4([CH2:66][N:42]([C:40]([C:38]5[N:39]=[C:35]([CH:32]([CH3:33])[CH3:34])[S:36][CH:37]=5)=[O:41])[CH2:43][CH2:44][O:45]4)[CH2:49]3)[CH:53]=2)[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]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 669637513-(3-(2-(8-(2-Isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoic acid trifluoroacetate salt

Product 1

HCID 58168503N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

HATU (0.201 g) was added in one portion to a stirred solution at 0° C. of 3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoic acid trifluoroacetate salt (0.25 g) (example 176 step h), N-(2,2-dimethoxy ethyl)cyclohexanamine (0.076 g) (WO2008075025) and triethylamine (0.283 ml) in DMF (4 mL) at 0° C. The mixture was stirred at 20° C. for 3 hours and then partitioned between ethyl acetate and brine, the organic layer was washed with brine (×2), dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.270 g.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washthe organic layer was washed with brine (×2)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e6f1a6b9477c46f0b4a76f5d4efceeb7
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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