L-Alaninol → 3-(Tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-(4-methoxy-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide
Reaction equation
N[C@@H:2]([CH3:5])[CH2:3][OH:4].[NH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Cl.F[C:15]1[CH:16]=[C:17]([C@@H:23]([C:25]2[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=2)[NH2:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].Cl.COC1[CH:39]=[CH:38][C:37]([C@@H:40]([C:42]2C=N[N:45]([CH3:47])[CH:46]=2)N)=CC=1>>[CH3:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([C@H:23]([NH:24][C:3]([C:2]2[CH:5]=[C:40]3[C:37](=[CH:38][CH:39]=2)[CH:47]=[N:45][C:46]([NH:6][CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:42]3)=[O:4])[C:25]2[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=2)=[CH:16][CH:15]=1Participants
Reactant 4
Product 1
Procedure
3-(Tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-(4-methoxy-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide (II-10) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with 4-amino-tetrahydropyran and in step 5, 50c was replaced with (S)-(4-methoxy-phenyl)(1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride (50i). 1H NMR (400 MHz, DMSO-d6) δ 9.17 (d, J=8.6 Hz, 1H), 8.90 (s, 1H), 8.08 (s, 1H), 7.83 (d, J=8.6 Hz, 1H), 7.54 (dd, J=8.5, 1.4 Hz, 1H), 7.51 (s, 1H), 7.35 (d, J=8.6 Hz, 2H), 7.32 (s, 1H), 6.91 (d, J=8.6 Hz, 2H), 6.71 (s, 1H), 6.50 (d, J=8.0 Hz, 1H), 6.26 (d, J=8.6 Hz, 1H), 3.93-3.86 (m, 2H), 3.86-3.80 (m, 1H), 3.79 (s, 3H), 3.74 (s, 3H), 3.44 (td, J=11.5, 2.0 Hz, 2H), 1.92 (d, J=10.6 Hz, 2H), 1.49 (ddd, J=15.5, 12.0, 4.3 Hz, 2H).
Sources & evidence
- ORD record
- ord-438cb371f3004379929f6b9dc9f3919a
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388171B2
Reaction notes
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