Triethylamine → (9-(4-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 1689230Notes

Reaction equation

HRID 1689230 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[N:13]=1.C(N(CC)CC)C.Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][OH:44])=[CH:38][CH:37]=1>C(#N)C>[OH:44][CH2:43][CH2:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][N:24]2[CH2:25][CH2:26][C:20]3([O:19][CH2:18][CH2:17][N:16]([C:14]([C:12]4[N:13]=[C:9]([CH3:8])[S:10][CH:11]=4)=[O:15])[CH2:21]3)[CH2:22][CH2:23]2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223370184-(Bromomethyl)benzeneethanolHCID 66964121(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

Product 1

HCID 57988939(9-(4-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 4, step h) (0.791 g) and triethylamine (0.697 mL) in acetonitrile (10 mL) was added 2-(4-(bromomethyl)phenyl)ethanol (example 16, step a) and the resulting mixture stirred overnight. The solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate (25 mL) and saturated sodium bicarbonate solution (25 mL). The aqueous phase was separated and extracted with ethyl acetate (2×25 mL). The combined organic solutions were washed with brine (25 mL), dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a yellow oil. Yield 0.76 g.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate (25 mL) and saturated sodium bicarbonate solution (25 mL)
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washThe combined organic solutions were washed with brine (25 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-559361a00e6a4923bee41fd29d6b1c3d
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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