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Toluene → N(2)-[4-(4-Methyl-piperazin-1-yl)-phenyl]-N(7)-phenyl-pyrrolo[2,1-f][1,2,4]triazine-2,7-diamine

HRID 1261876
ノート
印刷プレビュー

反応式

HRID 1261876 の反応式
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.C(Cl)Cl>[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[N:10]4[N:9]=3)=[CH:13][CH:14]=2)[CH2:19][CH2:20]1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 1140TolueneHCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 66711200(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

生成物 1

HCID 66711302N(2)-[4-(4-Methyl-piperazin-1-yl)-phenyl]-N(7)-phenyl-pyrrolo[2,1-f][1,2,4]triazine-2,7-diamine

試薬・触媒・溶媒 4

HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 887Methanol溶媒
HCID 6344Dichloromethane溶媒

実験手順

Into a Microwave vial, (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.12 g, 0.30 mmol), Aniline (0.0470 g, 0.504 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (0.0050 g, 0.0091 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.0051 g, 0.0055 mmol), Sodium tert-butoxide (0.0349 g, 0.363 mmol) were added and purged under an atmosphere of Nitrogen for 10 minutes. Toluene (1.00 mL, 9.39 mmol) was then added and stirred at room temperature for one minute. The reaction was microwaved on 300 watts, 150° C. for 20 minutes. HPLC suggested 50% conversion. DCM and methanol was added and purified via flash column chromatography with DCM and methanol as eluant (10% methanol). The solvent was removed under vacuum to afford a semi-solid. The semi-solid was purified via HPLC with water and ACN as eluant (5 to 45% ACN). The collected fractions afforded N(2)-[4-(4-Methyl-piperazin-1-yl)-phenyl]-N(7)-phenyl-pyrrolo[2,1-f][1,2,4]triazine-2,7-diamine as a yellow solid. MP 152-157° C. LCMS (E/I+) 400.18 (M+H). NMR 1H (DSMO-d6)-8.99 (s, 1H), 8.68 (s, 1H), 8.17 (s, 1H), 7.52 (d, 2H, J=8.96 Hz), 7.22 (t, 1H, J=7.92 Hz), 6.78-6.85 (m, 2H), 6.73 (d, 1H, J=9.00 Hz), 6.56 (d, 1H, J=4.65 Hz), 3.00 (t, 1H, J=4.25 Hz), 2.44 (bs, 4H), 2.23 (s, 3H), 1.16 (s, 9H).

後処理

  1. custompurged under an atmosphere of Nitrogen for 10 minutes
  2. customThe reaction was microwaved on 300 watts, 150° C. for 20 minutes
  3. custompurified via flash column chromatography with DCM and methanol as eluant (10% methanol)
  4. customThe solvent was removed under vacuum
  5. customto afford a semi-solid
  6. customThe semi-solid was purified via HPLC with water and ACN as eluant (5 to 45% ACN)

出典と根拠

ORDレコード
ord-c9080302d1af400c8d437cc049a58905
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08471005B2

反応ノート

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