1,8-Diazabicyclo(5.4.0)undec-7-ene → [3-(3-Bromo-imidazo[1,2-b]pyridazin-6-ylamino)-propyl]-methyl-carbamic acid tert-butyl ester

HRID 870638노트

반응식

HRID 870638 반응식
[Br:1][C:2]1[N:6]2[NH:7][C:8](=O)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:39]([O:43][C:44](=[O:51])[N:45]([CH2:47][CH2:48][CH2:49][NH2:50])[CH3:46])([CH3:42])([CH3:41])[CH3:40].N12CCCN=C1CCCCC2>CN(C=O)C.C(#N)C>[C:39]([O:43][C:44](=[O:51])[N:45]([CH2:47][CH2:48][CH2:49][NH:50][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([Br:1])=[CH:3][N:4]=2)[N:7]=1)[CH3:46])([CH3:42])([CH3:40])[CH3:41]

참가 물질

7

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2756543tert-butyl N-(3-aminopropyl)-N-methylcarbamateHCID 606230023-Bromoimidazo[1,2-b]pyridazin-6-ol

생성물 1

HCID 86696332[3-(3-Bromo-imidazo[1,2-b]pyridazin-6-ylamino)-propyl]-methyl-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

Acetonitrile (16.0 mL) was added to a mixture of 3-bromo-imidazo[1,2-b]pyridazin-6-one (344.3 mg, 1.6 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) [56602-33-6], the mixture allowed to stir to effect dissolution. A solution of (3-amino-propyl)-methyl-carbamic acid tert-butyl ester [150349-36-3] (0.8 g, 3.98 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) [6674-22-2] (2.4 mL, 2.4 mmol) in DMF (4.0 mL) was added and the reaction allowed to stir at ambient temperature for 3d. The reaction solution was partitioned between brine and ethyl acetate, dried (MgSO4), and flash chromatographed (silica gel, eluted with 10% (v/v) 2-propanol/ethyl acetate) to provide [3-(3-bromo-imidazo[1,2-b]pyridazin-6-ylamino)-propyl]-methyl-carbamic acid tert-butyl ester as 0.4 g of clear yellow oil. LRMS (ESI) m/z 384.1/386.1 [(M+H)]+, calc'd for C16H22BrN6O2: 384.28.

후처리

  1. dissolutiondissolution
  2. customThe reaction solution was partitioned between brine and ethyl acetate
  3. dry with materialdried (MgSO4), and flash
  4. customchromatographed
  5. wash(silica gel, eluted with 10% (v/v) 2-propanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-c737420ad69e45499736b237e998bba4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

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