(2S)-(-)-1-Amino-3-phenoxy-2-propanol → HCID 178444750, compound

HRID 1370225Notes

Reaction equation

HRID 1370225 reaction equation
[CH2:1]([NH:7][C:8]1[S:9][C:10](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[C:11](=[O:13])[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:28][CH2:29][C@H:30]([OH:39])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:1]([NH:7][C:8]1[S:9][C:10](=[CH:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH2:26][CH2:25][CH:24]([NH:28][CH2:29][C@H:30]([OH:39])[CH2:31][O:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:23][CH2:22]3)=[CH:19][CH:20]=2)[C:11](=[O:13])[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 1133101(2S)-(-)-1-Amino-3-phenoxy-2-propanol2×HCID 178444752HCID 178444752, compound2×

Product 1

HCID 178444750HCID 178444750, compound

Procedure

The title compound was prepared from 1-[4-(2-hexylamino-4-oxo-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one(which was obtained in Intermediate 32) and (2S)-1-amino-3-phenoxy-propan-2-ol(which was obtained in Intermediate 3) according to the procedure of Example 1 as a yellowish solid; mp 182-184° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 0.87(t, J=6.5 Hz, 3 H), 1.20-1.40 (m, 10H), 1.50-1.65 (m, 2 H), 1.80-1.95 (m, 2 H), 2.60-4.00(m, 10H), 6.85-6.95(m, 3 H), 7.02 (d, J=9.0 Hz, 2 H), 7.20-7.35 (m, 2 H), 7.40 (d, J=9.0 Hz, 2 H), 7.45 (s, 1 H), 9.62 (brs, 1 H); MS (ES) m/z: 269.1 ((M+2 H)2+, 100%), 537.1(MH+, 20%); HRMS Calcd. for C30H41N4O3S (MH+): 537.2899. Found: 537.2875.

Sources & evidence

ORD record
ord-f29fc0fb83db413589c17dd6ca8d3499
Source dataset
uspto-grants-2003_06
Patent number
US06583140B2

Reaction notes

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