1-Methoxy-2-propanol → HCID 66711160, compound

HRID 1261915Notes

Reaction equation

HRID 1261915 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.[N:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.COCC(O)C.C(N(CC)C(C)C)(C)C>>[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:36][C:33]3[CH:34]=[CH:35][C:30]([O:29][CH2:28][CH2:27][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[CH:31][CH:32]=3)=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 64847114-(2-Morpholinoethoxy)anilineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711160HCID 66711160, compound

Procedure

Into a Microwave vial, [A] 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.116 g, 0.000404 mol), [B] 4-(2-Morpholin-4-yl-ethoxy)-phenylamine (0.197 g, 0.000888 mol), 1-Methoxy-2-propanol (0.971 mL, 0.00993 mol) and N,N-Diisopropylethylamine (0.155 mL, 0.000888 mol) were added. The reaction was microwaved on 300 watts, 170° C. for 50 minutes. The solvent was removed under vacuum. The desired product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 12% methanol). The collected fractions afforded [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine a yellow solid (22 mg, 12%). MP 125-126° C. LCMS (E/I+) 446.8 (M+H). NMR 1H (DSMO-d6)-9.20 (s, 1H), 8.91 (s, 1H), 7.79 (dd, 1H, JJ=1.60, 6.04 Hz), 7.61 (d, 2H, J=9.00 Hz), 7.45 (dt, 1H, JJ=1.40, 7.12 Hz), 7.21 (d, 1H, J=8.36 Hz), 7.12 (t, 1H, J=7.53 Hz), 6.92 (d, 1H, J=4.56 Hz), 6.89 n (d, 1H, J=4.64 Hz), 6.80 (d, 2H, J=9.00 Hz), 4.02 (t, 2H, J=5.80 Hz), 3.79 (s, 3H), 3.3.58 (t, 4H, J=4.68 Hz), 2.65 (t, 2H, J=5.68 Hz), 2.46 (t, 4H, J=4.48 Hz).

Workup

  1. customThe reaction was microwaved on 300 watts, 170° C. for 50 minutes
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d497d94ab8ae4305a9bef66fd328e1b3
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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