L-Alaninol → HCID 86712013, compound
Reaction equation
N[C@@H:2]([CH3:5])[CH2:3][OH:4].[NH2:6][CH:7]1[CH2:11][CH2:10][O:9][CH2:8]1.Cl.FC1C=[C:16]([C@@H:22]([C:24]2C=N[N:27]([CH3:29])[CH:28]=2)N)[CH:17]=[CH:18]C=1OC.Cl.[F:31][C:32]1[CH:33]=[C:34]([C@@H:40]([C:42]2[CH:46]=[CH:45][N:44]([CH3:47])[N:43]=2)[NH2:41])[CH:35]=[CH:36][C:37]=1[O:38][CH3:39]>>[F:31][C:32]1[CH:33]=[C:34]([CH:40]([NH:41][C:3]([C:2]2[CH:5]=[C:22]3[C:16](=[CH:17][CH:18]=2)[CH:29]=[N:27][C:28]([NH:6][CH:7]2[CH2:11][CH2:10][O:9][CH2:8]2)=[CH:24]3)=[O:4])[C:42]2[CH:46]=[CH:45][N:44]([CH3:47])[N:43]=2)[CH:35]=[CH:36][C:37]=1[O:38][CH3:39]Participants
Procedure
3-(Tetrahydro-furan-3-ylamino)-isoquinoline-6-carboxylic acid [(3-fluoro-4-methoxy-phenyl)-(1-methyl-1H-pyrazol-3-yl)-methyl]-amide (II-52) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with 3-amino-tetrahydrofuran and in step 5, (S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride was replaced with (S)-(3-fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-3-yl)methanamine hydrochloride (50d). 1H NMR (500 MHz, DMSO-d6): δ 9.26 (d, J=9.0 Hz, 1H), 8.93 (s, 1H), 8.28 (s, 0.4H), 8.12 (s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.63 (s, 1H), 7.62-7.55 (m, 1H), 7.47-7.25 (m, 1H), 7.18 (d, J=9.0 Hz, 1H), 7.14-7.10 (m, 1H), 6.82 (d, J=6.0 Hz, 1H), 6.70 (s, 1H), 6.32 (d, J=9.0 Hz, 1H), 6.20 (s, 1H), 4.31-4.29 (m, 1H), 3.95-3.92 (m, 1H), 3.88-3.72 (m, 8H), 3.61-3.58 (m, 1H), 2.50-2.20 (m, 1H), 1.84-1.76 (m, 1H).
Sources & evidence
- ORD record
- ord-c337f9a3fabf4dd7988f9426ceb600ea
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388171B2
Reaction notes
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