Hydrogen Bromide → 4-Cyclohexyl-5-{2-[3-(2-diethylamino-ethylamino)phenylamino]-5-methyl-pyrimidin-4-yl}2-methylsulfanylthiophene-3-carbonitrile

HRID 478193

反応式

HRID 478193 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([S:20][CH3:21])=[C:17]([C:22]#[N:23])[C:16]=3[CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:12]([CH3:30])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:31]([N:33]([CH2:37][CH3:38])[CH2:34][CH2:35]Br)[CH3:32].Br.CC(C)([O-])C.[Na+]>C1COCC1.C(Cl)Cl.CO>[CH:24]1([C:16]2[C:17]([C:22]#[N:23])=[C:18]([S:20][CH3:21])[S:19][C:15]=2[C:13]2[C:12]([CH3:30])=[CH:11][N:10]=[C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:32][CH2:31][N:33]([CH2:37][CH3:38])[CH2:34][CH3:35])[CH:3]=3)[N:14]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

8

反応物 4

HCID 260Hydrogen BromideHCID 706082-Bromo-N,N-diethylethanamineHCID 220190265-[2-(3-Aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrileHCID 23676156Sodium t-butoxide

生成物 1

HCID 220190444-Cyclohexyl-5-{2-[3-(2-diethylamino-ethylamino)phenylamino]-5-methyl-pyrimidin-4-yl}2-methylsulfanylthiophene-3-carbonitrile収率 33%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-[2-(3-aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile (20 mg, 45.91 micromol) and N,N-diethyl-2-amino-bromoethane.HBr (12 mg, 45.91 micromol) in THF was added sodium t-butoxide (9 mg, 91.82 micromol) and the eaction was stirred at ambient temperature overnight. TLC indicated conversion to product (10% MeOH:CH2Cl2). The reaction was partitioned between EtOAc and water, the organics were dried over sodium sulfate then concentrated in vacuo. The crude product was purified by chromatography (silica gel, 5% MeOH:CH2Cl2) to afford VI-26 in 33% yield. δ0.95 (bs, 6H), 1.0-1.8 (m, 10H), 2.0 (s, 3H), 2.6 (s, 3H), 2.75 (bs, 2H), 3.4 (s, 1H), 3.6 (bs, 2H), 4.0 (bs, 2H), 5.2 (s, 1H), 6.5 (d, 1H), 6.55 (s, 1H) , 6.6 (d, 1H) , 7.0 (t, 1H) , 8.1 (s, 1H).

後処理

  1. customThe reaction was partitioned between EtOAc and water
  2. dry with materialthe organics were dried over sodium sulfate
  3. concentrationthen concentrated in vacuo
  4. customThe crude product was purified by chromatography (silica gel, 5% MeOH:CH2Cl2)
  5. customto afford VI-26 in 33% yield

出典と根拠

ORDレコード
ord-c2642cf063e74035a11283f366eaf23b
出典データセット
uspto-grants-2003_11
特許番号
US06642227B2

関連ノート

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