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Hydrochloric Acid → 6-(3-(2,4-Difluorophenyl)-1-(pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1929994
ノート
印刷プレビュー

反応式

HRID 1929994 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=3)[N:19]=2)=[CH:12][N:11]([CH:26]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]2)[N:10]=1.FC1C=C(F)C=CC=1C1N(C2CCN(C(OC(C)(C)C)=O)C2)N=CC=1C1C=CC2N(C(C(C)C)=NN=2)N=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH:23]([CH3:24])[CH3:25])=[N:21][N:22]=3)[N:19]=2)=[CH:12][N:11]([CH:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)[N:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 57929860tert-butyl 3-(3-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)pyrrolidine-1-carboxylateHCID 57929884tert-butyl 3-(5-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate

生成物 1

HCID 579298656-(3-(2,4-Difluorophenyl)-1-(pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine
収率 74%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

To a round bottom flask was added tert-butyl 3-(3-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate and tert-butyl 3-(5-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate (0.446 g, 0.875 mmol, Preparation #X.1.1.1) as a mixture of regioisomers followed by 1,4-dioxane (10 mL) and concentrated hydrochloric acid (3.50 mL, 17.5 mmol). The reaction mixture was heated to about 85° C. for about 20 min. The reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM (50 mL). The organic layer was isolated and the aqueous layer extracted with DCM (2×50 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The reaction mixture was purified by flash chromatography (40 g RediSep® silica gel; DCM/MeOH with 5% 2.0 M ammonia in EtOH gradient from 1:0 to 80:20) to give the title compound (0.265 g, 74%): LC/MS (Table 1, Method g) Rt=1.75 min; MS m/z: 410.3 (M+H)+.

後処理

  1. additionas a mixture of regioisomers
  2. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM (50 mL)
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer extracted with DCM (2×50 mL)
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe reaction mixture was purified by flash chromatography (40 g RediSep® silica gel; DCM/MeOH with 5% 2.0 M ammonia in EtOH gradient from 1:0 to 80:20)

出典と根拠

ORDレコード
ord-907de110e8174209ad6c033d6c937c42
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188083B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート