Tetrahydrofuran → [5-{[2-({4-[(Diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxoquinolin-1(4H)-yl]acetic acid

HRID 1948107노트

반응식

HRID 1948107 반응식
C([O:3][C:4](=[O:47])[CH2:5][N:6]1[C:15]2[C:10](=[C:11]([NH:16][C:17]3[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[C:19]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([CH2:34][P:35]([O:40][CH2:41][CH3:42])([O:37][CH2:38][CH3:39])=[O:36])=[CH:30][C:29]=4[O:43][CH3:44])[N:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:45])[C:8]([CH3:46])=[CH:7]1)C.C1COCC1.O[Li].O>CO>[CH2:41]([O:40][P:35]([CH2:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:19]2[N:18]=[C:17]([NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:10]=3[C:9](=[O:45])[C:8]([CH3:46])=[CH:7][N:6]4[CH2:5][C:4]([OH:47])=[O:3])[C:22]([C:23]([F:24])([F:26])[F:25])=[CH:21][N:20]=2)=[C:29]([O:43][CH3:44])[CH:30]=1)([O:37][CH2:38][CH3:39])=[O:36])[CH3:42]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 58292890ethyl[5-{[2-({4-[(diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxoquinolin-1(4H)-yl]acetate

생성물 1

HCID 58293027[5-{[2-({4-[(Diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxoquinolin-1(4H)-yl]acetic acid수율 61%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of ethyl[5-{[2-({4-[(diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxoquinolin-1(4H)-yl]acetate (Example 300, 41 mg, 0.061 mmol) in MeOH (0.5 mL), and THF (0.5 mL) was charged with LiOH H2O (25.6 mg, 0.61 mmol). The resulting mixture was stirred at room temperature for 5 h. The reaction mixture was concentrated under reduced pressure. The material was purified by prep TLC (5% MeOH in DCM) to give 24.1 mg of the desired product (yield: 61%). 1H NMR (DMSO-d6, 400 MHz): δ=1.20 (m, 6H), 1.99 (s, 3H), 3.24 (d, J=21.2 Hz, 2H), 3.78 (s, 3H), 3.99 (m, 2H), 6.90 (d, 1H), 7.03 (s, 1H), 7.43 (s, br, 1H), 7.61 (d, J=7.2 Hz, 1H), 7.94 (s, br, 1H). 8.36 (s, 1H), 8.51-8.56 (m, 2H). MS (ES+): m/z 651.19 [MH+]. HPLC: tR=1.32 min (UPLC TOF, polar—3 min).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe material was purified by prep TLC (5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-846e16c2a725476fac0275f88be886c6
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399433B2

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