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

HRID 446486Notes

Reaction equation

HRID 446486 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]([OH:62])=O)[CH2:47]3)[O:45][CH2:44][CH2:43]2)=[O:41])[N:39]=1)([CH3:34])[CH3:33].[CH2:67]([NH:69][CH2:70][CH:71]([O:74][CH3:75])[O:72][CH3:73])[CH3:68].C(N(CC)CC)C>CN(C=O)C>[CH3:73][O:72][CH:71]([O:74][CH3:75])[CH2:70][N:69]([CH2:67][CH3:68])[C:60](=[O:62])[CH2:59][CH2:58][O:57][CH2:56][CH2:55][C:54]1[CH:63]=[CH:64][CH:65]=[C:52]([CH2:51][CH2:50][N:48]2[CH2:49][C:46]3([CH2:66][N:42]([C:40]([C:38]4[N:39]=[C:35]([CH:32]([CH3:33])[CH3:34])[S:36][CH:37]=4)=[O:41])[CH2:43][CH2:44][O:45]3)[CH2:47]2)[CH:53]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3020444N-ethyl-2,2-dimethoxyethanamineHCID 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 58168544N-(2,2-dimethoxyethyl)-N-ethyl-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 b), N-ethyl-2,2-dimethoxyethanamine (0.059 g) (U.S. Pat. No. 2,707,186) and triethylamine (0.283 ml) in DMF (4 mL). The mixture was stirred at 20° C. for 3 hours and then partitioned between ethyl acetate and aq brine, the organic layer was washed with brine (×2), dried, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.250 g.

Workup

  1. custompartitioned between ethyl acetate and aq 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-0c8b3901230e4718b1df6a28de77b310
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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