Dimethylformamide → HCID 58292876、化合物

HRID 511385

反応式

HRID 511385 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:13][C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:17]=[C:16]([NH:24][C:25]3[CH:39]=[CH:38][C:28]([CH2:29][P:30](=[O:37])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])=[CH:27][CH:26]=3)[N:15]=2)=[C:6]2[C:10]=1[CH2:9][N:8]([CH3:11])[C:7]2=[O:12].[CH3:40][N:41](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:40]([C:2]1[CH:3]=[CH:4][C:5]([NH:13][C:14]2[C:19]([C:20]([F:22])([F:21])[F:23])=[CH:18][N:17]=[C:16]([NH:24][C:25]3[CH:39]=[CH:38][C:28]([CH2:29][P:30](=[O:37])([O:31][CH2:32][CH3:33])[O:34][CH2:35][CH3:36])=[CH:27][CH:26]=3)[N:15]=2)=[C:6]2[C:10]=1[CH2:9][N:8]([CH3:11])[C:7]2=[O:12])#[N:41]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 58292897Diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate

生成物 1

HCID 58292876HCID 58292876、化合物

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

A mixture of diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate (20.0 mg, 0.0318 mmol), zinc cyanide (3.74 mg, 0.0318 mmol), Pd(PPh3)4 (5.52 mg, 0.00477 mmol) in DMF (0.5 mL) was evacuated and purged with N2 three times. The mixture was irradiated in a microwave reactor at 150° C. for 5 minutes. The crude mixture was passed though a Thiol-SPE cartridge to remove Pd and subsequently purified by MDP. The title compound was obtained as white solid (13.5 mg, 74% yield). 1H NMR (400 MHz, CDCl3) δ=1.29 (t, J=7.1 Hz, 6 H), 3.20 (d, J=21.5 Hz, 2 H), 3.24 (s, 3 H), 4.09 (quin, J=7.3 Hz, 4 H), 4.54 (s, 2 H), 7.31-7.39 (m, 2 H), 7.49 (d, J=8.1 Hz, 2 H), 7.56 (br. s., 1 H), 7.70 (d, J=8.8 Hz, 1 H), 8.44 (s, 1 H), 8.70 (d, J=8.3 Hz, 1 H), 10.85 (s, 1 H). MS (ES+): m/z 575.21 (100) [MH+]; HPLC: tR=1.08 min (UPLC, purity).

後処理

  1. customwas evacuated
  2. custompurged with N2 three times
  3. customThe mixture was irradiated in a microwave reactor at 150° C. for 5 minutes
  4. customto remove Pd
  5. customsubsequently purified by MDP

出典と根拠

ORDレコード
ord-4d132607e87045b88499aab66e5580f2
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

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