1-Methoxy-2-propanol → HCID 86661699, 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:23]=[C:24]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[O:34][C:27]1([CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)[CH:26]=[CH:25]2.C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH3:39][O:38][C:37]1[CH:36]=[C:35]2[C:24]([CH:25]=[CH:26][C:27]3([O:34]2)[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]3)=[CH:23][C:22]=1[NH:21][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]=1Participants
Procedure
A slurry of 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (78.0 mg, 0.271 mmol), 6-Amino-7-methoxy-1′-methyl-spiro[chromene-2,4′-piperidin]-4-((3H)-one (151 mg, 0.546 mmol)) and N,N-Diisopropylethylamine (0.150 mL, 0.861 mmol) in 1-Methoxy-2-propanol (0.300 mL, 3.07 mmol) was irradiated in a CEM microwave (200° C., 60 min). Purification by prep HPLC afforded 7-methoxy-6-{[7-(2-methoxyphenyl)pyrrolo[2,1-f][1,2,4]triazin-2-yl]amino}-1′-methylspiro[chromene-2,4′-piperidin]-4-((3H)-one trifluoroacetic acid salt (13 mg; Yield=7.8%). 1H-NMR (DMSO-d6): 9.41 (br s, 1H), 8.93 (s, 1H), 8.16 (s, 1H), 7.82 (m, 2H), 7.39 (m, 1H), 7.18 (d, 1H, J=8.3 Hz), 7.07 (m, 1H), 6.99 (d, 1H, J=4.2 Hz), 6.94 (d, 1H, J=4.2 Hz), 6.79 (s, 1H), 3.93 (s, 3H), 3.79 (s, 3H), 3.34 (m, 2H), 3.20 (m, 2H), 2.84 (s, 3H), 2.82 (s, 2H), 2.17 (m, 2H), 1.87 (m, 2H). LCMS (HPLC): m/z=550 (M+H).
Workup
- customPurification by prep HPLC
Sources & evidence
- ORD record
- ord-17a6a166f1e2421f85a66e2dbd2eb881
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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