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1-Methylpiperazine → 4-tert-Butyl-N-(3-(6-(4-(1-(isopropyl(methyl)amino)-2-(4-methylpiperazin-1-yl)-2-oxoethyl)phenylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl)benzamide

HRID 1363506
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HRID 1363506 반응식
[C:1]([C:5]1[CH:44]=[CH:43][C:8]([C:9]([NH:11][C:12]2[C:13]([CH3:42])=[C:14]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH:31]([N:35]([CH:37]([CH3:39])[CH3:38])[CH3:36])[C:32](O)=[O:33])=[CH:27][CH:26]=4)[C:21](=[O:40])[N:20]([CH3:41])[CH:19]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:1]([C:5]1[CH:44]=[CH:43][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:26]=[CH:27][C:28]([CH:31]([N:35]([CH:37]([CH3:38])[CH3:39])[CH3:36])[C:32]([N:49]5[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]5)=[O:33])=[CH:29][CH:30]=4)[C:21](=[O:40])[N:20]([CH3:41])[CH:19]=3)[C:13]=2[CH3:42])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576251502-(4-{6-[3-(4-tert-Butylbenzamido)-2-methylphenyl]-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino}phenyl)-2-[isopropyl(methyl)amino]acetic Acid

생성물 1

HCID 57625169
4-tert-Butyl-N-(3-(6-(4-(1-(isopropyl(methyl)amino)-2-(4-methylpiperazin-1-yl)-2-oxoethyl)phenylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl)benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a sealed tube equipped with a magnetic stirrer, were charged 29 (100 mg, 0.168 mmol), 1-methylpiperazine (14.6 mg, 0.168 mmol), DMF (3 mL), Hunig's base (65.1 mg, 0.503 mmol), and BOP (74.3 mg, 0.168 mmol). The reaction mixture was stirred at room temperature for 26 hrs. Most solvent was removed by rotary evaporation and the resulting residue was dissolved in ethyl acetate (100 mL). The solution was washed with water (15 mL×3), dried over MgSO4, filtered and solvent removed in vacuo. Silica gel column chromatography (MeOH:CH2Cl2=5:95) afforded 30 as a light yellow solid, 25 mg (22%). 1H NMR (300 MHz, CDCl3) δ8.45 (s, 1 H), 8.09 (s, 1 H), 7.95 (s, 1 H), 7.92 (s, 1 H), 7.85 (m, 2 H), 7.75 (m, 1 H), 7.54 (s, 1 H), 7.51 (s, 1 H), 7.40 (m, 2 H), 7.19-7.23 (m, 2 H), 6.79 (s, 1 H), 5.19 (s, 1 H), 3.62 (s, 3 H), 3.40 (broad s, 2 H), 3.21 (broad s, 2 H), 2.26-2.50 (m, 9 H), 2.18 (s, 3 H), 1.92 (broad s, 2 H), 1.34 (s, 9 H), 1.25-1.31 (m, 6 H) ppm; MS (ESI+) m/z 678.19 (M+H).

후처리

  1. customTo a sealed tube equipped with a magnetic stirrer
  2. customMost solvent was removed by rotary evaporation
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (100 mL)
  4. washThe solution was washed with water (15 mL×3)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent removed in vacuo

출처 및 근거

ORD 기록
ord-9fe90f91adf44caea8f3fbb2be5d084f
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07884108B2

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