Acetic Acid → 6-Benzylamino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796610노트

반응식

HRID 1796610 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.[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:29]([NH:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 221794876-Amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride

생성물 1

HCID 221794806-Benzylamino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

6-Amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride (10 mg, 0.026 mmol), benzaldehyde (2.8 mg, 0.026 mmol) and acetic acid (0.5 ml) in 1,2-dichloroethane (1.0 ml) were stirred at RT. After 20 minutes, NaBH(OAc)3 was added and the reaction mixture was stirred for additional 15 minutes, quenched with saturated NH4OH (4.0 ml), extracted with dichloromethane (3×3 ml), dried over Na2SO4, concentrated and purified by silica gel flash chromatography to isolate 376 as a yellow film (1.3 mg, 11%). [M+H]+=446.2.

후처리

  1. customquenched with saturated NH4OH (4.0 ml)
  2. extractionextracted with dichloromethane (3×3 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-5814a9eee7ec4b4e9ef03320efeef437
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030112B2

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