L-Alaninol → HCID 86712008, compound

HRID 1051372Notes

Reaction equation

HRID 1051372 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]([C@H:40]([C:42]2[CH:46]=[CH:45][N:44]([CH3:47])[N:43]=2)[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])[CH:35]=[CH:36][C:37]=1[O:38][CH3:39]

Participants

5

Reactant 4

HCID 80307L-AlaninolHCID 3365553Oxolan-3-amineHCID 86712001(S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochlorideHCID 86712009HCID 86712009, compound

Product 1

HCID 86712008HCID 86712008, compound

Procedure

N—((R)-(3-Fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-3-yl)methyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide (II-27) 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 (R)-(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 Hz, 1H), 8.92 (s, 1H), 8.45 (s, 0.4H), 8.28 (s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.62 (d, J=2 Hz, 1H), 7.56 (dd, J=8.55, 1.5 Hz, 1H), 7.26 (dd, J=12.5, 1.5 Hz, 1H), 7.18 (d, J=9 Hz, 1H), 7.12 (t, J=9 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 6.70 (s, 1H), 6.32 (d, J=9 Hz, 1H), 6.20 (d, J=2 Hz, 1H), 4.30 (m, 1H), 3.94 (m, 1H), 3.85 (q, J=7.5 Hz, 1H), 3.81 (s, 3H), 3.80 (s, 3H), 3.75 (m, 1H), 3.59 (dd, J=8.5, 3.5 Hz, 1H), 2.22 (m, 1H), 1.87 (m, 1H).

Sources & evidence

ORD record
ord-8b2cbb118e0f44aaa8c7fe46f20c27e0
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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