L-Alaninol → HCID 73335847, compound

HRID 1051373Notes

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[N:46]([CH3:47])[N:45]=[CH:44][CH: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[N:46]([CH3:47])[N:45]=[CH:44][CH: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

Reactant 4

HCID 80307L-Alaninol

HCID 3365553Oxolan-3-amine

HCID 86712001(S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride

HCID 86712011HCID 86712011, compound

Product 1

HCID 73335847HCID 73335847, compound

Procedure

N—((S)-(3-Fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-5-yl)methyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide (II-31) 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)-(3-fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-5-yl)methanamine hydrochloride (50f). 1H NMR (500 MHz, DMSO-d6) δ 9.46 (s, J=6.5 Hz, 1H), 8.93 (s, 1H), 8.13 (s, 1H), 7.87 (d, J=8.0 Hz, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.34-7.17 (m, 4H), 6.84 (d, J=6.0 Hz, 1H), 6.70 (s, 1H), 6.49 (d, J=8.5 Hz, 1H), 5.95 (d, J=1.5 Hz, 1H), 4.40 (m, 1H), 3.94 (m, 1H), 3.88-3.83 (m, 4H), 3.76-3.74 (m, 4H), 3.59 (m, 1H), 2.20 (m, 1H), 1.89 (m, 1H).

Sources & evidence

ORD record: ord-0c0e381f44e24cd7aa36131ad76b3477
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388171B2

Reaction notes

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