Citric Acid → N-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-methanesulfonamide

HRID 1796656노트

반응식

HRID 1796656 반응식
Cl.[NH2:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1.CN1CCOCC1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:25]([C:9]1[CH:8]=[N:7][N:6]2[CH:27]=[C:3]([NH:2][S:37]([CH3:36])(=[O:39])=[O:38])[C:4]([CH3:28])=[C:5]2[C:10]=1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)#[N:26]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 221794876-Amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride

생성물 1

HCID 22179430N-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-methanesulfonamide수율 45.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a slurry of 6-amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride (Example 11B) (14 mg, 0.035 mmol) in CH2Cl2 (2 ml) was added N-methyl morpholine (12.3 μl, 0.113 mmol) followed by MsCl (4.5 μl, 0.057 mmol). The reaction mixture was stirred overnight, 10% citric acid (3 ml) was added. The resulting mixture was extracted with CHCl3 (10 ml), the organic layer was separated and dried with Na2SO4, concentrated to give the title compound (6.9 mg, 45%). It has a retention time of 6.01 min (standard LCl method, 8 min run). MS Found: (M+H)+=434.0

후처리

  1. extractionThe resulting mixture was extracted with CHCl3 (10 ml)
  2. customthe organic layer was separated
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-43f5fc4c0bba46a3aad598eaec6dcdc2
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030112B2

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