Trifluoroacetic acid → HCID 58447636, 화합물

HRID 1036245노트

반응식

HRID 1036245 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]C(C)(C)C)=O)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.[NH2:29][C:30]1[N:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][N:39]([C:42](=[O:44])[CH3:43])[CH2:38][CH2:37]2)=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(Cl)Cl>[C:42]([N:39]1[CH2:38][CH2:37][N:36]([C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:15](=[O:17])[CH2:14][C:11]3[CH:12]=[N:13][C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=4)=[N:9][CH:10]=3)=[N:35][CH:34]=2)[CH2:41][CH2:40]1)(=[O:44])[CH3:43]

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 284116891-(4-(6-Aminopyridin-3-YL)piperazin-1-YL)ethan-1-oneHCID 58447797Tert-butyl 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetate

생성물 1

HCID 58447636HCID 58447636, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of tert-butyl 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetate 183-4 (35 mg, 0.12 mmol) and TFA (0.5 mL) in DCM (3 mL) was stirred at room temperature for 2 hours. The solvents were evaporated to dryness under high vacuum. The crude product, 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetic acid 183-5, was dissolved in DMF (2 mL). 1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethanone (35 mg, 0.16 mmol) and DIEA (107 uL, 0.61 mmol) were added to the solution before O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (70 mg, 0.18 mmol). The mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetamide 183. MS m/z 433.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.47 (s, 2H), 8.50 (d, 1H), 8.22 (s, 1H), 8.14 (d, 1H), 7.97 (d, 1H), 7.87 (d, 1H), 7.38 (dd, 1H), 3.83 (s, 2H), 3.68 (t, 2H), 3.64 (t, 2H), 3.15 (t, 2H), 3.09 (t, 2H), 2.58 (s, 3H), 2.09 (s, 3H).

후처리

  1. customThe solvents were evaporated to dryness under high vacuum
  2. dissolutionThe crude product, 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetic acid 183-5, was dissolved in DMF (2 mL)
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe solvent was removed by rotary evaporation
  5. customThe crude product was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-370b3f381ba949bb8bf03c1123c5d2d4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546396B2

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