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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-4-(morpholinomethyl)thiazol-2-amine

HRID 1684954
ノート
印刷プレビュー

反応式

HRID 1684954 の反応式
[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)[CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:24][C:21]2[S:22][CH:23]=[C:19]([CH2:18][N:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)[N:20]=2)=[N:4][CH:3]=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

7

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 21253444-(Morpholin-4-ylmethyl)-1,3-thiazol-2-amineHCID 23676156Sodium t-butoxideHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazine

生成物 1

HCID 57541337N-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-4-(morpholinomethyl)thiazol-2-amine収率 27%

試薬・触媒・溶媒 2

HCID 72499888Dibenzalacetone palladium触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

Intermediate 3 (5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, 140 mg, 0.50 mmol), Intermediate 6 (4-(1-morpholinomethyl) thiazol-2-ylamine, 120 mg, 0.60 mmol), sodium tert-butoxide (68 mg, 0.71 mmol), palladium dibenzylidene acetone (19 mg, 0.02 mmol) and Xantphos (23 mg, 0.04 mmol) were suspended in toluene (4 mL). The mixture is degassed with nitrogen for 5 min and then stirred at 90° C. for 16 h. The solvent is evaporated in vacuo to leave a brown residue. The residue is purified by column chromatography, eluting with 2% methanolic ammonia (7 N) in dichloromethane to give the title compound as a yellow powder (53 mg, 27%). 1H NMR (400 MHz, d6-DMSO) δ 2.53 (s, 4H, CH2CH2), 3.51 (s, 2H, CH2), 3.61 (m, 4H, CH2CH2), 6.99 (s, 1H), 8.13 (s, 1H), 8.61 (s, 1H), 8.75 (s, 1H).

後処理

  1. customThe mixture is degassed with nitrogen for 5 min
  2. customThe solvent is evaporated in vacuo
  3. customto leave a brown residue
  4. customThe residue is purified by column chromatography
  5. washeluting with 2% methanolic ammonia (7 N) in dichloromethane

出典と根拠

ORDレコード
ord-f85e440e0c1a4d139be12b587a351691
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08148369B2

反応ノート

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