Trifluoroacetic acid → 8-(3-aminophenyl)-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 527406노트

반응식

HRID 527406 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH:16][C:17]1[N:18]=[CH:19][C:20]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([C:28]3[CH:29]=[C:30]([NH:34]C(=O)OC(C)(C)C)[CH:31]=[CH:32][CH:33]=3)[C:21]=2[N:22]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:34][C:30]1[CH:29]=[C:28]([N:23]2[C:21]3[N:22]=[C:17]([NH:16][C:4]4[CH:5]=[CH:6][C:7]([N:9]5[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]5)=[CH:8][C:3]=4[O:2][CH3:1])[N:18]=[CH:19][C:20]=3[CH:26]=[CH:25][C:24]2=[O:27])[CH:33]=[CH:32][CH:31]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86732016tert-butyl (3-(2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

생성물 1

HCID 867320178-(3-aminophenyl)-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The crude 1a from above was treated with DCM (20 mL) and TFA (20 mL) and stirred at RT for 30 min. The reaction mixture was concentrated under reduced pressure (rotary evaporator) and purified on a silica gel column (1-20% 2M NH3/MeOH in DCM) affording 8-(3-aminophenyl)-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one (1b) (470 mg, 1.03 mmol, 79% yield) as a brown amorphous solid. m/z (ESI, +ve ion) 458.0 (M+H)+. 1H NMR (400 MHz, MeOH-d4) δ ppm 8.67 (1H, s), 7.88 (1H, d, J=9.4 Hz), 7.63 (1H, d, J=8.2 Hz), 7.32 (1H, t, J=8.0 Hz), 6.91 (1H, dd, J=8.1, 1.5 Hz), 6.59-6.65 (2H, m), 6.53-6.59 (1H, m), 6.46-6.52 (1H, m), 6.24 (1H, br. s.), 3.88 (3H, s), 3.21 (4H, br. s.), 2.84 (4H, br. s.), 2.53 (3H, s).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure (rotary evaporator)
  2. custompurified on a silica gel column (1-20% 2M NH3/MeOH in DCM)

출처 및 근거

ORD 기록
ord-e21867c83cec4a1c8a772d807bfbdfe4
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346801B2

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