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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
Notes
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Reaction equation

HRID 1261876 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 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

Product 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

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 887MethanolSolvent
HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c9080302d1af400c8d437cc049a58905
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08471005B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes