L-Alaninol → N-((S)-1-(3-Fluoro-4-methoxyphenyl)-2-hydroxyethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide
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.[NH2:31][C@@H:32]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([F:43])[CH:36]=1)[CH2:33][OH:34]>>[F:43][C:37]1[CH:36]=[C:35]([C@H:32]([NH:31][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])[CH2:33][OH:34])[CH:40]=[CH:39][C:38]=1[O:41][CH3:42]Participants
5
Reactant 4
Product 1
Procedure
N—((S)-1-(3-Fluoro-4-methoxyphenyl)-2-hydroxyethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide (II-26) 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)-2-amino-2-(3-fluoro-4-methoxyphenyl)ethanol hydrochloride (62d) 1H NMR (500 MHz, CD3OD) δ 8.89 (s, 1H), 8.09 (s, 1H), 7.89 (d, J=8.5 Hz, 1H), 7.59 (d, J=6.5 Hz, 1H), 7.22-7.19 (m, 2H), 7.09 (t, J=8.5 Hz, 1H), 6.80 (s, 1H), 5.18 (m, 1H), 4.42 (m, 1H), 4.07-3.99 (m, 2H), 3.92-3.85 (m, 6H), 3.76 (m, 1H), 2.38 (m, 1H), 1.98 (m, 1H).
Sources & evidence
- ORD record
- ord-01a5347d6cfe47c89c8dd7f7b826e86e
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388171B2
Reaction notes
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