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Sodium Azide → 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carbonyl azide

HRID 1925120
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HRID 1925120 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]4[N:15]([CH:17]=[C:18]([C:20](O)=[O:21])[N:19]=4)[N:16]=3)[C:6]=2[CH:23]=1.C(N(C(C)C)C(C)C)C.[N-:33]=[N+:34]=[N-:35].[Na+].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]4[N:15]([CH:17]=[C:18]([C:20]([N:33]=[N+:34]=[N-:35])=[O:21])[N:19]=4)[N:16]=3)[C:6]=2[CH:23]=1
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반응물 4

HCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 592332496-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylic acid

생성물 1

HCID 592330636-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carbonyl azide

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 22728543Water ethylacetate용매

실험 절차

To a stirred solution of 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylic acid 13B (3.6 g, 9.65 mmol), N-ethyl-N-isopropylpropan-2-amine (7.48 g, 57.9 mmol) and sodium azide (6.27 g, 96 mmol) in anhydrous DMF (60 mL), PyBOP (6.02 g, 11.58 mmol) was added in portions at ambient temperature over 5 min. The reaction was stirred for another 30 min and then poured into a EtOAc/H2O (100/300 mL) mixture and shaken well. The resulting precipitate was filtered, rinsed with H2O followed by EtOAc, and dried in vacuum over P2O5 for 18 hrs to provide the title compound, 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carbonyl azide 13C (2.1 g, 5.28 mmol, 55%). The EtOAc solution washed with 5% citric acid (2×100 mL), NaHCO3, dried with MgSO4, filtered and concentrated to dryness to give additional crude product (1.6 g of 80% pure material). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.28 (s, 2 H) 7.37 (d, J=9.60 Hz, 1 H) 7.59 (dd, J=8.84, 1.77 Hz, 1 H) 8.09 (d, J=8.84 Hz, 1 H) 8.26 (d, J=10.10 Hz, 1 H) 8.32 (d, J=1.26 Hz, 1 H) 8.92 (s, 1H). MS:m/z 398.2 (M+H)+.

후처리

  1. stirringshaken well
  2. filtrationThe resulting precipitate was filtered
  3. washrinsed with H2O
  4. dry with materialdried in vacuum over P2O5 for 18 hrs

출처 및 근거

ORD 기록
ord-5fb3b02946b4482689fd3791c6a52c8f
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178534B2

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