Diisopropylethylamine → HCID 66711116, compound

HRID 1261962Notes

Reaction equation

HRID 1261962 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]3)[CH2:9]2)=[CH:4][C:3]=1[O:23][CH3:24].CS([C:28]1[N:33]=[CH:32][C:31]2=[CH:34][CH:35]=[C:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[N:30]2[N:29]=1)=O.C(N(CC)C(C)C)(C)C>COCCO.CO>[CH3:24][O:23][C:3]1[CH:4]=[C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([N:14]3[CH2:15][CH2:16][N:17]([C:20](=[O:22])[CH3:21])[CH2:18][CH2:19]3)[CH2:9]2)[CH:6]=[CH:7][C:2]=1[NH:1][C:28]1[N:33]=[CH:32][C:31]2=[CH:34][CH:35]=[C:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[N:30]2[N:29]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 66710849HCID 66710849, compound

Product 1

HCID 66711116HCID 66711116, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1-{4-[1-(4-amino-3-methoxy-phenyl)-piperidin-3-yl]-piperazin-1-yl}-ethanone (80 mg, 0.24 mmol) and 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (46 mg, 0.16 mmol) in 2-methoxyethanol (0.50 mL) and treated with N,N-Diisopropylethylamine (56 μL, 0.32 mmol). The reaction was microwaved on 300 watts, 200 C for 9.5 hours. The sample was diluted with methanol (10 mL), filtered and concentrated. The crude product was purified by RF-HPLC to afford 34 mg of the title compound as an amber powder after lyophyllization. MS=556 (M-TFA+1); NMR (DMSO-d6, ppm): 9.83 (br, 1H), 8.91 (s, 1H), 7.86 (m, 2H), 7.56 (s, 1H), 7.45 (t, J=7 Hz, 1H), 7.20 (d, J=7 Hz, 1H), 7.10 (t, J=7 Hz, 1H), 6.95 (q, J=5 Hz, 14 Hz, 2H), 6.69 (s, 1H), 6.46 (d, J=7 Hz, 1H), 3.87 (s, 3H), 3.80 (s, 3H), 3.50 (m, 4H), 2.91 (t, J=12 Hz, 2H), 2.70 (t, J=10 Hz, 2H), 2.33 (m, 1H), 2.13 (m, 2H), 2.07 (s, 3H), 1.89 (m, 1H), 1.64 (t, J=10 Hz, 2H).

Workup

  1. customThe reaction was microwaved on 300 watts, 200 C for 9.5 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by RF-HPLC

Sources & evidence

ORD record
ord-5d6a172d60ee4e3aa56c6698eb625189
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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