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

HRID 478193

반응식

HRID 478193 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c2642cf063e74035a11283f366eaf23b
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642227B2

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