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2-(Pyridin-2-yl)but-3-yn-2-ol → (+/-)-8-Fluoro-9-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

HRID 575089
ノート
印刷プレビュー

反応式

HRID 575089 の反応式
Br[C:2]1[C:3]([F:19])=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[S:10][C:9]([C:15]([NH2:17])=[O:16])=[N:8][C:7]=3[C:6]=2[CH:18]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([OH:30])([C:28]#[CH:29])[CH3:27]>CS(C)=O.C(N(CC)CC)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:19][C:3]1[C:2]([C:29]#[C:28][C:26]([OH:30])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)[CH3:27])=[CH:18][C:6]2[C:7]3[N:8]=[C:9]([C:15]([NH2:17])=[O:16])[S:10][C:11]=3[CH2:12][CH2:13][O:14][C:5]=2[CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 167625022-(Pyridin-2-yl)but-3-yn-2-olHCID 866930599-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

生成物 1

HCID 86693118(+/-)-8-Fluoro-9-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 679
Dimethyl Sulfoxide
溶媒
HCID 8471Triethylamine溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

The title compound was prepared according to a procedure similar to that described in Procedure G. Into a 8-mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed a suspension 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (200 mg, 0.58 mmol, 1.00 equiv), 2-(pyridin-2-yl)but-3-yn-2-ol (300 mg, 2.04 mmol, 3.50 equiv) and Pd(PPh3)2Cl2 (200 mg, 0.28 mmol, 0.50 equiv) in DMSO (0.5 mL) and triethylamine (0.5 mL). The final reaction mixture was irradiated with microwave radiation for 3 h at 70° C. The resulting solution was diluted with 50 mL of ethyl acetate. The resulting mixture was washed with 3×25 mL of water. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-016(Waters)): Column, XSelect Prep C18; mobile phase, water with 0.05% NH3H2O and CH3CN (23% CH3CN up to 63% in 10 min, hold 3 min); Detector, uv 254/220 nm. This resulted in 18 mg (7%) of 8-Fluoro-9-(3-hydroxy-3-pyridin-2-yl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide as a light yellow solid. LC-MS (ES, m/z): 410[M+H]+; 1H-NMR (400 MHz, DMSO-d6, ppm) δ 8.657 (d, 1H), 8.574 (d, 1H), 8.482 (s, 1H), 7.884 (m, 2H), 7.792 (d, 1H), 7.352 (m, 1H), 7.020 (d, 1H), 6.383 (s, 1H), 4.386 (t, 2H), 3.408 (t, 2H), 1.841 (s, 3H).

後処理

  1. customInto a 8-mL sealed tube
  2. custompurged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. customThe final reaction mixture
  5. customwas irradiated with microwave radiation for 3 h at 70° C
  6. washThe resulting mixture was washed with 3×25 mL of water
  7. dry with materialThe mixture was dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-016(Waters))
  10. waithold 3 min
  11. customThis resulted in 18 mg (7%) of 8-Fluoro-9-(3-hydroxy-3-pyridin-2-yl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide as a light yellow solid

出典と根拠

ORDレコード
ord-b8137d7907604af8bc06a013a114c7ae
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09034866B2

反応ノート

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