Triethylamine → (9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isobutylthiazol-4-yl)methanone

HRID 471191노트

반응식

HRID 471191 반응식
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:25]1[C:30]2([CH2:35][CH2:34][N:33]([CH2:36][C:37]3[CH:38]=[C:39]([CH2:43][CH2:44][OH:45])[CH:40]=[CH:41][CH:42]=3)[CH2:32][CH2:31]2)[CH2:29][NH:28][CH2:27][CH2:26]1.[CH2:46]([C:50]1[S:51][CH:52]=[C:53]([C:55](O)=[O:56])[N:54]=1)[CH:47]([CH3:49])[CH3:48].C(N(CC)CC)C>CN(C=O)C>[OH:45][CH2:44][CH2:43][C:39]1[CH:38]=[C:37]([CH:42]=[CH:41][CH:40]=1)[CH2:36][N:33]1[CH2:32][CH2:31][C:30]2([O:25][CH2:26][CH2:27][N:28]([C:55]([C:53]3[N:54]=[C:50]([CH2:46][CH:47]([CH3:49])[CH3:48])[S:51][CH:52]=3)=[O:56])[CH2:29]2)[CH2:35][CH2:34]1

참가 물질

6

반응물 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 235881542-(2-Methylpropyl)-1,3-thiazole-4-carboxylic acidHCID 579893852-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenyl)ethanol

생성물 1

HCID 57989287(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isobutylthiazol-4-yl)methanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.34 g) was added to a solution of 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenyl)ethanol (example 82, step a) (0.2 g), 2-isobutylthiazole-4-carboxylic acid (0.13 g) and triethylamine (0.38 mL) in DMF (7 mL) at 0° C. The resulting yellow solution was allowed to warm to RT and was stirred for 2 h. The mixture was partitioned between ethyl acetate (100 mL) and brine (100 mL), the organic phase was washed with brine (2×100 mL), dried over sodium sulphate, filtered and the solvent evaporated. The resulting gum was purified by silica gel chromatography eluting with 47.5:47.5:5 isohexane:ethyl acetate:triethylamine to 95:5 ethyl acetate:triethylamine gradient. The fractions containing product were combined, toluene (200 mL) was added, and the solvent evaporated under reduced pressure to give the subtitled compound as a clear gum. Yield 0.2 g.

후처리

  1. customThe mixture was partitioned between ethyl acetate (100 mL) and brine (100 mL)
  2. washthe organic phase was washed with brine (2×100 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe resulting gum was purified by silica gel chromatography
  7. washeluting with 47.5:47.5:5 isohexane
  8. additionThe fractions containing product
  9. additiontoluene (200 mL) was added
  10. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-e4f18b4fff4a4aeba64d88b30444f1b0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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