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Dichloromethane → Azepan-1-yl-(5-pyridin-4-yl-thiophen-3-yl)-methanone

HRID 1914554
ノート
印刷プレビュー

反応式

HRID 1914554 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)=[CH:3][CH:2]=1.[N:15]1([C:22](=O)[CH3:23])[CH2:21][CH2:20][CH2:19]NCC1.[CH3:25]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(Cl)Cl>CC#N>[N:15]1([C:12]([C:9]2[CH:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[S:11][CH:10]=2)=[O:14])[CH2:21][CH2:20][CH2:19][CH2:25][CH2:23][CH2:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 4186202N-AcetylhomopiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581102285-Pyridin-4-yl-thiophene-3-carboxylic acid

生成物 1

HCID 44224462Azepan-1-yl-(5-pyridin-4-yl-thiophen-3-yl)-methanone収率 28.8%

試薬・触媒・溶媒

1
HCID 6342Acetonitrile溶媒

実験手順

5-Pyridin-4-yl-thiophene-3-carboxylic acid (0.4 mmol) was dissolved in MeCN (2 mL). 1-[1,4]Diazepan-1-yl-ethanone (1.8 mmol), and HATU (0.4 mmol) were added and the reaction mixture stirred for 72 hours. DCM (20 mL) was added and the organic solution was separated and the solvent removed by evaporation. The residue was purified by HPLC, eluting with 10%-90% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum and freeze-dried to give the title compound as a white solid (33 mg). LCMS m/z 287.09 [M+H]+ RT=5.20 min. (Analytical Method 2). 1H NMR (400 MHz, MeCN-d): δ 8.6 (d, 2H), 7.95 (d, 2H), 7.9 (s, 1H), 7.8 (s, 1H), 3.6 (t, 2H), 3.5 (t, 2H), 1.8-1.6 (m, 6H).

後処理

  1. customthe organic solution was separated
  2. customthe solvent removed by evaporation
  3. customThe residue was purified by HPLC
  4. washeluting with 10%-90% acetonitrile in water (0.1% formic acid) over 30 minutes
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum
  7. customfreeze-dried

出典と根拠

ORDレコード
ord-72e456684d454ab8ab41a2981dbf7f33
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08614209B2

反応ノート

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