Methanol → Trifluoroacetic acid

HRID 475925

반응식

HRID 475925 반응식
Cl[C:2]1[N:3]=[C:4]([NH:21][CH3:22])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[N:32]1[CH:36]=[N:35][C:34]([CH3:37])=[N:33]1)[NH2:28].[OH:38]S(O)(=O)=O.[CH3:43][OH:44]>CN1C(=O)CCC1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:28][C:2]2[N:3]=[C:4]([NH:21][CH3:22])[C:5]3[CH2:10][CH2:9][CH:8]([C:11]4[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=4)[C:6]=3[N:7]=2)[CH:29]=[CH:30][C:31]=1[N:32]1[CH:36]=[N:35][C:34]([CH3:37])=[N:33]1.[C:43]([OH:38])([C:17]([F:20])([F:19])[F:18])=[O:44]

참가 물질

7

반응물 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 580756152-chloro-N-methyl-7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amineHCID 595778183-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline

생성물 2

HCID 6422Trifluoroacetic acid수율 42%HCID 58075478N2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-N4-methyl-7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2-chloro-N-methyl-7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (Preparation AZa) (8 mg, 0.024 mmol) and 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (4.97 mg, 0.024 mmol) in NMP (Volume: 48.7 μl) was added H2SO4 (1.686 0.032 mmol). The reaction mixture was stirred at 100° C. in a capped vial overnight. The reaction mixture was diluted with methanol and purified by reverse-phase preparative HPLC to afford N2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-N4-methyl-7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine, TFA (6.3 mg, 10.22 μmol, 42.0% yield). LC-MS (M+H)+=497.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 11.69 (1H, s), 9.32 (1H, s), 8.63 (1H, s), 7.94 (1H, d, J=6.7 Hz), 7.72-7.79 (2H, m), 7.59 (1H, s), 7.52 (1H, dd, J=8.7, 1.7 Hz), 5.79 (1H, d, J=4.9 Hz), 4.60-4.63 (1H, m), 3.99 (3H, s), 3.28 (3H, m), 2.97-3.01 (1H, m), 2.84-2.91 (2H, m), 2.64 (3H, s), 2.33-2.39 (1H, m), 1.27-1.33 (1H, m).

후처리

  1. custompurified by reverse-phase preparative HPLC

출처 및 근거

ORD 기록
ord-fcf4c86b2c354d6885adec96bef93ecc
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637525B2

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