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Nicotinic Acid → Phenyl-(4-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-piperazin-1-yl)-acetic acid methyl ester

HRID 1927614
ノート
印刷プレビュー

反応式

HRID 1927614 の反応式
[CH3:1][O:2][C:3](=[O:24])[CH:4]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:25](O)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:25]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[O:32])=[CH:21][CH:22]=2)[CH2:15][CH2:16]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 4

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69305249HCID 69305249、化合物

生成物 1

HCID 16665212Phenyl-(4-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-piperazin-1-yl)-acetic acid methyl ester収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of [4-(4-amino-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester (50 mg, 0.15 mmol), nicotinic acid (23 mg, 0.18 mmol), and HATU (70 mg, 0.18 mmol) in DMF (2 mL) was treated with iPr2NEt (32 μL, 0.18 mmol). After 16 h, the mixture was diluted with H2O and extracted with DCM. The organic layer was washed with satd. aq. NaHCO3 and brine, dried (MgSO4), and concentrated to give an oil, which was purified by PTLC to give a tan solid (51 mg, 77%). MS (ESI): mass calcd. for C25H26N4O3, 430.50; m/z found, 431.4 [M+H]+. 1H NMR (CDCl3): 9.07-9.06 (m, 1H), 8.77-8.76 (m, 1H), 8.20-8.18 (m, 1H), 8.01 (s, 1H), 7.68 (br s, 1H), 7.51-7.42 (m, 4H), 7.38-7.32 (m, 3H), 6.92-6.90 (m, 2H), 4.06 (s, 1H), 3.71 (s, 3H), 3.22-3.20 (m, 4H), 2.64-2.62 (m, 4H).

後処理

  1. extractionextracted with DCM
  2. washThe organic layer was washed with satd
  3. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by PTLC

出典と根拠

ORDレコード
ord-bdcc361d72ac485a9f1aa2b0206316b0
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08183239B2

反応ノート

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