Diisopropylethylamine → HCID 66711542, compound

HRID 1261934Notes

Reaction equation

HRID 1261934 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14](S(C)=O)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[N:29]1([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1>COCCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:40][C:37]4[CH:36]=[CH:35][C:34]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:39][CH:38]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8088414-(Pyrrolidin-1-yl)anilineHCID 66710773HCID 66710773, compound

Product 1

HCID 66711542HCID 66711542, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

7-(3-Chloro-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (125.0 mg, 0.0004284 mol), N,N-Diisopropylethylamine (0.112 mL, 0.000643 mol) and 4-Pyrrolidin-1-yl-phenylamine (139 mg, 0.000857 mol) were dissolved in 2-Methoxyethanol (3.01 mL) and The reaction was microwaved on 300 watts, 180° C. for 40 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 26.91 mg of [7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-pyrrolidin-1-yl-phenyl)-amine as a lyophilized powder. (M+H)=390.09. 1H NMR (400 MHz, CDCl3) δ 9.63 (s, 1H), 8.63 (s, 1H), 8.32 (s, 1H), 7.84 (m, 1H), 7.76 (d, 2H, J=8.93 Hz), 7.48 (m, 2H), 7.34 (d, 2H, J=8.93 Hz), 7.21 (m, 1H), 7.18 (m, 1H), 3.66 (m, 4H), 2.25 (m, 4H).

Workup

  1. customThe reaction was microwaved on 300 watts, 180° C. for 40 minutes or until HPLC
  2. customconsumption of starting material
  3. customthe product was isolated
  4. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-83f5d40d05674ea18ebf907a9b26c4e6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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