1-Methoxy-2-propanol → HCID 66712318, compound
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.[NH2:21][C:22]1[CH:26]=[CH:25][N:24]([CH2:27][C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:29])[N:23]=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:21][C:22]3[CH:26]=[CH:25][N:24]([CH2:27][C:28]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[O:29])[N:23]=3)=[N:5]2)=[CH:10][CH:11]=1Participants
Procedure
Into a microwave vial, 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.150 g, 0.000522 mol), 2-(3-Amino-pyrazol-1-yl)-1-morpholin-4-yl-ethanone (0.241 g, 0.00115 mol), 1-Methoxy-2-propanol (1.26 mL, 0.0128 mol) and N,N-Diisopropylethylamine (0.200 mL, 0.00115 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 7% methanol). The collected fraction afforded a yellow solid (62 mg, 27%). LCMS (E/I+) 434.8 (M+H). MP 179-182° C. NMR 1H (DMSO-d6)-9.54 (s, 1H), 8.90 (s, 1H), 7.82 (dd, 1H, JJ=1.60, 7.70 Hz), 7.40-7.49 (m, 2H), 7.18 (d, 1H, J=8.23 Hz), 7.08 (t, 1H, J=7.64 Hz), 6.92 (d, 1H, J=4.70 Hz), 6.88 (, d, 1H, J=4.70 Hz), 6.43 (d, 1H, J=1.76 Hz), 3.78 (s, 3H), 3.52-3.62 (m, 4H), 3.39-3.52 (m, 4H), 3.30 (s, 3H).
Workup
- customThe reaction was microwaved on 300 watts, 170° C. for 50 minutes
- customThe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-d6116ddbb747445e8d054ead8cb8b057
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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