1-Methoxy-2-propanol → HCID 66710955, compound

HRID 1262021Notes

Reaction equation

HRID 1262021 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[OH:14])[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]([CH:13]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[OH:14])[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 66711148HCID 66711148, compound

Product 1

HCID 66710955HCID 66710955, compoundYield 4.7%

Procedure

(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl-methanol (86.0 mg, 0.299 mmol), 4-(4-morpholino)aniline (107 mg, 0.598 mmol) and N,N-Diisopropylethylamine (0.156 mL, 0.898 mmol) were suspended in 1-Methoxy-2-propanol (0.750 mL, 7.67 mmol) and the reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced under nitrogen. The crude reaction mixture was purified via Gilson reverse phase chromatography to afford 5.69 mg of [2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl-methanol as a lyophilized powder. (M+H)=402.1. 1H NMR (400 MHz, DMSO, d6) δ 9.49 (s, 1H), 9.16 (s, 1H), 7.79 (d, 2H, J=7.12 Hz), 7.67 (m, 1H), 7.58 (m, 2H), 7.50 (d, 2H, J=7.89 Hz), 7.11 (m, 1H), 6.89 (m, 1H), 6.75 (d, 2H, J=8.44 Hz), 3.73 (m, 4H), 3.30 (m, 1H), 3.02 (m, 4H).

Workup

  1. customthe reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC
  2. customconsumption of starting material
  3. customThe crude reaction mixture
  4. customwas purified via Gilson

Sources & evidence

ORD record
ord-fb57f79839f14db08fec74c5d750616a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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