Triethylamine → (9-(2-Fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(2,2,2-trifluoroethyl)thiazol-4-yl)methanone

HRID 471145Notes

Reaction equation

HRID 471145 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]([F:37])([F:36])[CH2:27][C:28]1[S:29][CH:30]=[C:31]([C:33]([OH:35])=O)[N:32]=1.[O:38]1[C:43]2([CH2:48][CH2:47][N:46]([CH2:49][C:50]3[C:51]([F:59])=[C:52]([CH2:56][CH2:57][OH:58])[CH:53]=[CH:54][CH:55]=3)[CH2:45][CH2:44]2)[CH2:42][NH:41][CH2:40][CH2:39]1.C(N(CC)CC)C>CN(C=O)C>[F:59][C:51]1[C:52]([CH2:56][CH2:57][OH:58])=[CH:53][CH:54]=[CH:55][C:50]=1[CH2:49][N:46]1[CH2:47][CH2:48][C:43]2([O:38][CH2:39][CH2:40][N:41]([C:33]([C:31]3[N:32]=[C:28]([CH2:27][C:26]([F:25])([F:37])[F:36])[S:29][CH:30]=3)=[O:35])[CH2:42]2)[CH2:44][CH2:45]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579889492-(2,2,2-Trifluoroethyl)-1,3-thiazole-4-carboxylic acidHCID 579891872-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol

Product 1

HCID 57989017(9-(2-Fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(2,2,2-trifluoroethyl)thiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.181 g) was added in one portion to a stirred solution at 0° C. of 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylic acid (example 67, step d) (0.077 g) and 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol (example 67, step f) (0.113 g) and triethylamine (0.153 mL) in DMF (5 mL). The reaction mixture was stirred at room temperature for 2 hours. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.180 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. washthe organic layer was washed twice with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-6dcb6bddd8a24a06a7b8f1c8e52e24a2
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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