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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
ノート
印刷プレビュー

反応式

HRID 1925120 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 22728543Water ethylacetate溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-5fb3b02946b4482689fd3791c6a52c8f
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178534B2

反応ノート

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