Triethylamine → (9-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-butylthiazol-4-yl)methanone

HRID 471176

Reaction equation

HRID 471176 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([C:29]1[S:30][CH:31]=[C:32]([C:34]([OH:36])=O)[N:33]=1)[CH2:26][CH2:27][CH3:28].[Si:37]([O:44][CH2:45][CH2:46][C:47]1[C:48]([F:65])=[C:49]([CH:62]=[CH:63][CH:64]=1)[CH2:50][N:51]1[CH2:61][CH2:60][C:54]2([O:59][CH2:58][CH2:57][NH:56][CH2:55]2)[CH2:53][CH2:52]1)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].C(N(CC)CC)C>CN(C=O)C>[Si:37]([O:44][CH2:45][CH2:46][C:47]1[C:48]([F:65])=[C:49]([CH:62]=[CH:63][CH:64]=1)[CH2:50][N:51]1[CH2:52][CH2:53][C:54]2([O:59][CH2:58][CH2:57][N:56]([C:34]([C:32]3[N:33]=[C:29]([CH2:25][CH2:26][CH2:27][CH3:28])[S:30][CH:31]=3)=[O:36])[CH2:55]2)[CH2:60][CH2:61]1)([C:40]([CH3:43])([CH3:41])[CH3:42])([CH3:39])[CH3:38]

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 140500762-Butyl-4-thiazolecarboxylic acidHCID 579891399-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Product 1

HCID 57989198(9-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-butylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.378 g) was added to a stirred solution of 2-butylthiazole-4-carboxylic acid (example 78, step g) (0.193 g), 9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 78, step d) (0.4 g), and triethylamine (0.383 g) in DMF (4 mL). After 1 h, the reaction mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water and brine, dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by silica gel chromatography eluting with 7:1:0.5, isohexane:ethyl acetate:triethylamine gave the subtitled compound as a gum. Yield 0.35 g.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed twice with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography
  7. washeluting with 7:1:0.5, isohexane

Sources & evidence

ORD record
ord-c054dffbc2784939868821c43590fefd
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Linked notes

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