1-Methoxy-2-propanol → HCID 66711002, compound

HRID 1262014Notes

Reaction equation

HRID 1262014 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:6]2[N:5]=1)=O.[CH2:21]1[N:26]([C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:25][CH2:24][O:23][CH2:22]1.C(N(CC)C(C)C)(C)C.COCC(O)C>>[N:26]1([C:27]2[CH:28]=[CH:29][C:30]([NH:33][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([CH2:13][NH:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[N:6]4[N:5]=3)=[CH:31][CH:32]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 81531DiisopropylethylamineHCID 66711343HCID 66711343, compound

Product 1

HCID 66711002HCID 66711002, compoundYield 30.5%

Procedure

(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl)-phenyl-amine (40.0 mg, 0.140 mmol), 4-(4-morpholino)aniline (49.8 mg, 0.279 mmol) and N,N-Diisopropylethylamine (0.0730 mL, 0.419 mmol) were dissolved in 1-Methoxy-2-propanol (0.50 mL, 5.1 mmol) and the reaction was irradiated at 300 watts, 200° C. for 20 minutes or longer depending on HPLC monitoring. The reaction was then reduced under nitrogen. The crude reaction mixture was purified via Gilson reverse phase chromatography. Combined fractions were lyophilized to afford 17.12 mg of (4-Morpholin-4-yl-phenyl)-(7-phenylaminomethyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine as a TFA salt. (M+H)=401.16. 1H NMR (400 MHz, DMSO, d6) δ 9.32 (s, 1H), 8.87 (s, 1H), 7.72 (d, 2H, J=8.29 Hz), 7.09 (t, 2H, J=7.32 Hz), 6.97 (m, 2H), 6.76 (m, 1H), 6.67 (m, 3H), 6.60 (t, 1H, J=7.32 Hz), 4.59 (s, 2H), 3.77 (m, 4H), 3.12 (m, 4H).

Workup

  1. customthe reaction was irradiated at 300 watts, 200° C. for 20 minutes or longer
  2. customThe crude reaction mixture
  3. customwas purified via Gilson

Sources & evidence

ORD record
ord-843b8a28f4724f6d9059978a59796f87
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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