L-Alaninol → N-((S)-1-(3-Fluorophenyl)-2-hydroxyethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide

HRID 1051369Notes

Reaction equation

HRID 1051369 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][CH:38]=[C:37]([F:41])[CH:36]=1)[CH2:33][OH:34]>>[F:41][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][CH:38]=1

Participants

5

Reactant 4

HCID 80307L-AlaninolHCID 3365553Oxolan-3-amineHCID 68088895(S)-2-amino-2-(3-fluorophenyl)ethanol hydrochlorideHCID 86712001(S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride

Product 1

HCID 73335753N-((S)-1-(3-Fluorophenyl)-2-hydroxyethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide

Procedure

N—((S)-1-(3-Fluorophenyl)-2-hydroxyethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide (II-20) 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 (S)-2-amino-2-(3-fluorophenyl)ethanol hydrochloride (62a). 1H NMR (500 MHz, DMSO-d6) δ 8.94 (s, 1H), 8.87 (d, J=8 Hz, 1H), 8.13 (s, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.56 (d, J=8.5 Hz, 1H), 7.38 (m, 1H), 7.26 (d, J=8.0 Hz, 2H), 7.08 (t, J=19.5 Hz, 1H), 6.84 (d, J=6 Hz, 1H), 6.72 (s, 1H), 5.12 (m, 1H), 5.02 (t, J=11.5 Hz, 1H), 4.32 (t, J=6.0, 1H), 3.96-3.93 (m, 1H), 3.87 (m, 1H), 3.78-3.67 (m, 3H), 3.61 (m, 1H), 2.23 (m, 1H), 1.98 (m, 1H).

Sources & evidence

ORD record
ord-b45e6a8d460042ffb30991cbe78b2207
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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