(2S)-(-)-1-Amino-3-phenoxy-2-propanol → HCID 178483522, compound

HRID 2416077Notes

Reaction equation

HRID 2416077 reaction equation
[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:10](=[O:12])[N:11]=1.[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>>[CH3:27][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([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)[CH2:22][CH2:21]3)=[CH:18][CH:19]=2)[C:10](=[O:12])[N:11]=1

Participants

3

Reactant 2

HCID 1133101(2S)-(-)-1-Amino-3-phenoxy-2-propanol2×HCID 178483524HCID 178483524, compound2×

Product 1

HCID 178483522HCID 178483522, compound

Procedure

The title compound was prepared from 1-{4-[2-(3-dimethylamino-propylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-phenyl}-piperidin-4-one(which was obtained in Intermediate 33) 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 166-168° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 10 H), 1.60-1.80 (m, 2 H), 1.80-2.00 (m, 2 H), 2.19 (s, 6 H), 2.25 (t, J=6.8 Hz, 2 H), 2.55-3.00(m, 5 H), 3.50-4.05(m, 7 H), 6.65-6.95(m, 3 H), 7.02 (d, J=9.0 Hz, 2 H), 7.20-7.30 (m, 2 H), 7.40 (d, J=9.0 Hz, 2 H), 7.48 (s, 1 H); MS (ES) m/z: 269.6 ((M+2H)2+, 100%), 538.1(MH+, 10%); HRMS Calcd. for C29H40N5O3S (MH+): 538.2852. Found: 538.2885.

Sources & evidence

ORD record
ord-e00d894a05884b89a070bc3c6e2b5560
Source dataset
uspto-grants-2004_11
Patent number
US06821991B2

Reaction notes

Loading…