Hydrochloric Acid → 3-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

HRID 870728ノート

反応式

HRID 870728 の反応式
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([Br:24])=[CH:22][N:23]=3)[N:20]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[ClH:1].[Br:24][C:21]1[N:19]2[N:20]=[C:15]([N:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)[CH:16]=[CH:17][C:18]2=[N:23][CH:22]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 686481214-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 866964333-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Concentrated hydrochloric acid (6.4 mL) was added to a solution of 4-(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester 2.9 g, 7.6 mmol) in methanol (150 mL), allowed to stir at ambient temperature overnight, then evaporated to dryness. The resultant yellow solid was dissolved in methanol and the stirred solution diluted with diethyl ether to precipitate 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride as 2.6 g of white powder, mp. 275-276° C. (dec.). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.24 (br. s., 4H) 3.82-3.92 (m, 4H) 7.57 (d, J=10.11 Hz, 1H) 8.05 (s, 1H) 8.12 (d, J=10.10 Hz, 1H) 9.70 (br. s., 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm 41.86, 42.37, 101.30, 114.15, 124.22, 127.20, 134.76, 155.43. LRMS (ESI) m/z 282.1/284.1 [(M+H)]+, calc'd for C10H12BrN5: 282.14.

後処理

  1. customevaporated to dryness
  2. dissolutionThe resultant yellow solid was dissolved in methanol
  3. additionthe stirred solution diluted with diethyl ether
  4. customto precipitate 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride as 2.6 g of white powder, mp. 275-276° C. (dec.)

出典と根拠

ORDレコード
ord-0892f9b3568a4f0599831a4389682aba
出典データセット
uspto-grants-2015_03
特許番号
US08969565B2

反応ノート

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