Trifluoroacetic acid → HCID 178511615, 화합물

HRID 1943435노트

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HRID 1943435 반응식
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([N:28]([CH:38]3[CH2:40][CH2:39]3)CC3C=CC(OC)=CC=3)[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=4)=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>CN1C(=O)CCC1.CO>[NH2:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:28][CH:38]3[CH2:39][CH2:40]3)[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=4)=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:6][CH2:7]1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 178490954HCID 178490954, 화합물

생성물 1

HCID 178511615HCID 178511615, 화합물수율 52.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

To 23C (0.464 mmol, 260 mg) in NMP (2 mL) was added TFA (0.2 mL). The resulting reaction mixture was heated at 100° C. for 24 hrs. The reaction mixture was diluted with MeOH and purified by HPLC Phenomenex Axia Luna 5 micron 30×100 mm) with 20% to 100% MeOH (0.1% TFA) in water (0.1% TFA) to isolate 6-((trans)-4-aminocyclohexylamino)-N-(2-chloropyridin-4-yl)-8-(cyclopropylamino)imidazo[1,2-b]pyridazine-3-carboxamide (107 mg, 0.243 mmol, 52.3% yield) as white solid. LC/MS (Phenomenex Luna 5 micron C18 4.6×30 mm, 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA). Rt=1.500 minutes. [M+H]=441.12. 1H NMR (400 MHz, MeOD) δ ppm 8.21-8.35 (1H, m), 8.01 (1H, s), 7.96 (1H, d, J=1.76 Hz), 7.33-7.51 (1H, m), 6.07 (1H, s), 3.60-3.85 (1H, m), 3.08-3.27 (1H, m), 2.49-2.66 (1H, m), 2.25-2.45 (2H, m), 2.06-2.28 (2H, m), 1.35-1.69 (4H, m), 0.77-0.97 (2H, m), 0.50-0.73 (2H, m).

후처리

  1. customThe resulting reaction mixture
  2. custompurified by HPLC Phenomenex Axia Luna 5 micron 30×100 mm) with 20% to 100% MeOH (0.1% TFA) in water (0.1% TFA)

출처 및 근거

ORD 기록
ord-e3155c3a8c264f8e92b45668f789bc4b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389527B2

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