4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → HCID 178518026, compound

HRID 1370208Notes

Reaction equation

HRID 1370208 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17](=[CH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:18](=[O:20])[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][CH2:36][C@H:37]([OH:47])[CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=1>>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[S:16][C:17](=[CH:21][C:22]3[CH:23]=[CH:24][C:25]([N:28]4[CH2:33][CH2:32][CH:31]([NH:35][CH2:36][C@H:37]([OH:47])[CH2:38][O:39][C:40]5[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=5)[CH2:30][CH2:29]4)=[CH:26][CH:27]=3)[C:18](=[O:20])[N:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenol2×HCID 178516398HCID 178516398, compound2×

Product 1

HCID 178518026HCID 178518026, compound

Procedure

The title compound was prepared from 1-{4-[2-(1-benzyl-piperdin-4-ylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-phenyl}-piperidin-4-one (which was obtained in Intermediate 21) and 4-[(2S)-3-amino-2-hydroxy-propoxyl]-phenol (which was obtained in Intermediate 5) according to the procedure of Example 1 as a pale yellowish solid; mp >175° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2 H), 1.40-1.65 (m, 2 H), 1.70-2.00 (m, 4 H), 2.06 (brt, J=9.5 Hz, 2 H), 2.55-2.95 (m, 6 H), 3.47 (s, 2 H), 3.70-4.00 (m, 5H), 4.92 (brs, 1 H), 6.66 (d, J=6.8 Hz, 2 H), 6.75 (d, J=6.8 Hz, 2 H), 7.02 (d, J=9.0 Hz, 2 H), 7.20-7.50 (m, 8H), 8.89 (brs, 1 H), 9.29 (brs, 1 H); MS (ES) m/z:321.6 ((M+2 H)2+, 100%); 642.1 (MH+, 5%); HRMS Calcd. for C36H44N5O4S (MH+): 642.3114. Found: 642.3095.

Sources & evidence

ORD record
ord-aff892ff6a5a4ed1970eec39d7bb811b
Source dataset
uspto-grants-2003_06
Patent number
US06583140B2

Reaction notes

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