Water → 6-chloro-8-(5-fluoropyridin-2-ylamino)-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

HRID 1943421

반응식

HRID 1943421 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[H-].[Na+].Br[C:12]1[C:13]2[N:14]([C:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][C:26]=3[F:31])=[O:23])=[CH:20][N:21]=2)[N:15]=[C:16]([Cl:18])[CH:17]=1.O>CN(C=O)C>[Cl:18][C:16]1[CH:17]=[C:12]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)[C:13]2[N:14]([C:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][C:26]=3[F:31])=[O:23])=[CH:20][N:21]=2)[N:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27377012-Amino-5-fluoropyridineHCID 596244958-Bromo-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

생성물 1

HCID 596249056-chloro-8-(5-fluoropyridin-2-ylamino)-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide수율 84.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-fluoropyridin-2-amine (20.63 mg, 0.184 mmol) in DMF (1 mL) was added 60% NaH (7.36 mg, 0.184 mmol). The mixture was stirred for 10 min until cessation of H2 evolution. 8A (24 mg, 0.074 mmol) was added. The mixture was stirred at room temperature overnight. Water was added, and the yellow solid was collected by filtration and dried to give 16A (25.2 mg, 57%). [M+H]=4 01. HPLC Peak Rt=3.345 minutes (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm.).

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationthe yellow solid was collected by filtration
  3. customdried

출처 및 근거

ORD 기록
ord-ee37ea45002c431e8230dc54bdfa6a23
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389527B2

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