L-Alaninol → N-((S)-2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide

HRID 1051370Notes

Reaction equation

HRID 1051370 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])=[CH:37][CH:36]=1)[CH2:33][OH:34]>>[OH:34][CH2:33][C@@H:32]([NH:31][C:3]([C:2]1[CH:5]=[C:22]2[C:16](=[CH:17][CH:18]=1)[CH:29]=[N:27][C:28]([NH:6][CH:7]1[CH2:11][CH2:10][O:9][CH2:8]1)=[CH:24]2)=[O:4])[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1

Participants

5

Reactant 4

HCID 80307L-AlaninolHCID 3365553Oxolan-3-amineHCID 70141372(S)-2-Amino-2-(4-methoxyphenyl)ethanol hydrochlorideHCID 86712001(S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride

Product 1

HCID 73335754N-((S)-2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide

Procedure

N—((S)-2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide (II-21) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with 3-amino-tetrahydrofuran and in step 5, 50c was replaced with 62c. 1H NMR (500 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.78 (d, J=8 Hz, 1H), 8.10 (s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.55 (dd, J=8.5, 1.5 Hz, 1H), 7.33 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 6.82 (d, J=6.0 Hz, 1H), 6.70 (s, 1H), 5.04 (m, 1H), 4.91 (t, J=6.0 Hz, 1H), 4.30 (m, 1H), 3.95 (m, 1H), 3.86 (m, 1H), 3.77-3.64 (m, 5H), 3.62-3.60 (m, 2H), 2.23 (m, 1H), 1.87 (m, 1H).

Sources & evidence

ORD record
ord-da120f262e7d4c4e8ef30b3605349b6e
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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