4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → HCID 178484377, compound

HRID 2188294Notes

Reaction equation

HRID 2188294 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:9](=[O:11])[N:10]=1)=[NH:4].[NH2:27][CH2:28][C@H:29]([OH:39])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1>>[OH:39][C@H:29]([CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[CH2:28][NH:27][CH:22]1[CH2:23][CH2:24][N:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:12]=[C:8]3[S:7][C:6]([NH:5][C:3](=[NH:4])[N:2]([CH3:1])[CH3:26])=[N:10][C:9]3=[O:11])=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenol2×HCID 178484381HCID 178484381, compound2×

Product 1

HCID 178484377HCID 178484377, compound

Procedure

The title compound was prepared from N,N-dimethyl-N′-{4-oxo-5-[4-(4-oxo-piperidin-1-yl)-benzylidene]-4,5-dihydro-thiazol-2-yl}-guanidine (which was obtained in Intermediate 23) and 4-((2S)-3-amino-2-hydroxy-propoxy)-phenol (which was obtained in Intermediate 5) according to the procedure of Example 1 as a yellowish solid; 1 H NMR (300 MHz, DMSO-d6) δ1.20-1.40 (m, 2 H), 1.75-1.95 (m, 2 H), 2.50-3.30 (m, 9 H), 3.70-3.90 (m, 7 H), 4.90 (brs, 1 H), 6.66 (d, J=6.8 Hz, 1 H), 6.74 (d, J=6.8 Hz, 1 H), 7.01 (d, J=8.8 Hz, 2 H), 7.41 (d, J=8.8 Hz, 2 H), 7.47 (s, 1 H); MS (ES) m/z: 270.0 ((M+2H)2+, 100%); 539.1 (MH+, 10%); HRMS Calcd. for C27H35N6O4S (MH+): 539.2441. Found: 539.2422.

Sources & evidence

ORD record
ord-1134ebc3ecd34f70a92d05b23caf455e
Source dataset
uspto-grants-2002_06
Patent number
US06410734B1

Reaction notes

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