Triethylamine → Benzo[b]thiophen-2-yl(9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 471179

반응식

HRID 471179 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:25]1[C:29]([C:30]([OH:32])=O)=[CH:28][C:27]2[CH:33]=[CH:34][CH:35]=[CH:36][C:26]1=2.[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>[S:25]1[C:29]([C:30]([N:56]2[CH2:55][C:54]3([CH2:53][CH2:52][N:51]([CH2:50][C:49]4[CH:62]=[CH:63][CH:64]=[C:47]([CH2:46][CH2:45][O:44][Si:37]([C:40]([CH3:42])([CH3:41])[CH3:43])([CH3:38])[CH3:39])[C:48]=4[F:65])[CH2:61][CH2:60]3)[O:59][CH2:58][CH2:57]2)=[O:32])=[CH:28][C:27]2[CH:33]=[CH:34][CH:35]=[CH:36][C:26]1=2

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579891399-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane

생성물 1

HCID 57989142Benzo[b]thiophen-2-yl(9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 benzo[b]thiophene-2-carboxylic acid (0.186 g), 9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 78, step d) (0.40 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 once with 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 0.38 g.

후처리

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed twice with water and once with 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

출처 및 근거

ORD 기록
ord-aedfab2623dd4f54a91c2800eed386d6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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