Diisopropylethylamine → HCID 66710910, compound

HRID 1261940Notes

Reaction equation

HRID 1261940 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.C(N(CC)C(C)C)(C)C.[NH2:30][C:31]1[CH:32]=[C:33]([N:37]2[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][OH:45])[CH2:39][CH2:38]2)[CH:34]=[CH:35][CH:36]=1>COCCO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:30][C:31]3[CH:32]=[C:33]([N:37]4[CH2:38][CH2:39][N:40]([CH2:43][CH2:44][OH:45])[CH2:41][CH2:42]4)[CH:34]=[CH:35][CH:36]=3)=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22330138HCID 22330138, compoundHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66710910HCID 66710910, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (150.0 mg, 0.0005220 mol), N,N-Diisopropylethylamine (0.136 mL, 0.000783 mol) and 2-[4-(3-Amino-phenyl)-piperazin-1-yl]-ethanol (231.0 mg, 0.001044 mol) were dissolved in 2-Methoxyethanol (3.66 mL) and the 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 provide 55.38 mg of 2-(4-{3-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanol as a lyophilated powder. (M+H)=445.21. 1H NMR (400 MHz, DMSO, d6) δ 9.16 (s, 1H), 8.94 (s, 1H), 7.72 (d, 1H, J=5.85 Hz), 7.44 (t, 1H, J=7.64 Hz), 7.26 (s, 1H), 7.19 (d, 1H, J=7.68 Hz), 7.08 (m, 2H), 7.01 (t, 1H, J=7.80 Hz), 6.90 (q, 2H, J=4.61 Hz), 6.46 (d, 1H, J=6.89 Hz), 3.76 (s, 3H), 3.53 (m, 4H), 3.04 (m, 2H), 2.87 (m, 2H), 2.67 (m, 2H), 2.44 (m, 2H).

Workup

  1. customthe The 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-2991669e7ff545c78203d94536c3b634
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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