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

HRID 1262258Notes

Reaction equation

HRID 1262258 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, compoundYield 28.2%

Procedure

Into a microwave vial, 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (128 mg, 0.445 mmol), 4-(2-Morpholin-4-yl-ethoxy)-phenylamine (198 mg, 0.891 mmol), 1-Methoxy-2-propanol (1.50 mL, 15.3 mmol) and N,N-Diisopropylethylamine (0.171 mL, 0.980 mmol) were added. The reaction was microwaved on 300 watts, 180° C. for 3 hours. The reaction was monitored by HPLC. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The Solvent was removed under vacuum. The desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methano). The collected fractions afforded a yellow solid (56 mg, 28%). LCMS (E/I+) 446.8 (M+H). MP 133-135° C. NMR 1H (DMSO-d6)-9.20 (s, 1H), 8.91 (s, 1H), 7.82 (m, 1H), 7.60 (d, 2H, 8.84 Hz), 7.45 (t, 1H, J=7.88 Hz), 6.92 (d, 1H, J=5.45 Hz), 6.80 (d, 1H, J=5.45 Hz), 6.79 (d, 2H, J=9.09 Hz), 4.02 (t, 2H, J=5.45 Hz), 3.82 (s, 3H), 3.58 (t, 4H, J=4.24 Hz), 2.65 (t, 2H, J=6.06 Hz), 2.46 (m, 4H).

Workup

  1. customThe reaction was microwaved on 300 watts, 180° C. for 3 hours
  2. customThe reaction was partitioned with water and DCM
  3. customThe organic was separated
  4. washwashed with Brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe solid was filtered
  7. washwashed with DCM
  8. customThe Solvent was removed under vacuum
  9. customThe desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methano)

Sources & evidence

ORD record
ord-ae0ff3abbf2e48728ca43a99a4f9cd32
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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