6-chloro-N-(3-fluoropyridin-4-yl)-8-(isoxazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamide → HCID 178522303, 화합물

HRID 1943463

반응식

HRID 1943463 반응식
Cl[C:2]1[CH:3]=[C:4]([NH:21][C:22]2[CH:26]=[CH:25][O:24][N:23]=2)[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[NH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]1>CN1C(=O)CCC1>[F:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[NH:13][C:11]([C:8]1[N:6]2[N:7]=[C:2]([NH:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]3)[CH:3]=[C:4]([NH:21][C:22]3[CH:26]=[CH:25][O:24][N:23]=3)[C:5]2=[N:10][CH:9]=1)=[O:12]

참가 물질

4

반응물 2

HCID 596247806-chloro-N-(3-fluoropyridin-4-yl)-8-(isoxazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamideHCID 178511715HCID 178511715, 화합물

생성물 1

HCID 178522303HCID 178522303, 화합물수율 61.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

A mixture of 6-chloro-N-(3-fluoropyridin-4-yl)-8-(isoxazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamide (20 mg, 0.054 mmol) and (trans)-4-aminocyclohexanol (61.6 mg, 0.535 mmol) in NMP (0.4 mL) was heated at 110° C. overnight. The reaction mixture was cooled to room temperature, and purified by reversed-phase preparative HPLC. The desired fractions were concentrated and dried to give 15 mg the title compound as a beige solid. HPLC Rt=2.615 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm), [M+1]=453.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified by reversed-phase preparative HPLC
  3. concentrationThe desired fractions were concentrated
  4. customdried

출처 및 근거

ORD 기록
ord-be5a1e2d52d744679539ac168f213b6b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389527B2

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