3-Amino-1,2-propanediol, (S)- → 2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(2-{[(2S)-2,3-dihydroxypropyl]amino}-1,3-thiazol-4-yl)pyridine-3,5-dicarbonitrile

HRID 1969495Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12](Br)[S:13][CH:14]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:3]=1.[NH2:32][CH2:33][C@H:34]([OH:37])[CH2:35][OH:36]>CC(C)=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([NH:32][CH2:33][C@H:34]([OH:37])[CH2:35][OH:36])[S:13][CH:14]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

100 mg (0.183 mmol) of 2-amino-4-(2-bromo-1,3-thiazol-4-yl)-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrile were initially charged in 2 ml of acetone, 834 mg (9.159 mmol) of (2S)-3-aminopropane-1,2-diol were added and the mixture was stirred at 80° C. for 12 h. A further 834 mg (9.159 mmol) of (2S)-3-aminopropane-1,2-diol were then added, and the mixture was stirred at 80° C. for a further 12 h. The reaction mixture was concentrated and the product was isolated by preparative HPLC. This gave 19 mg (19% of theory) of the target compound.

Workup

stirringthe mixture was stirred at 80° C. for a further 12 h
concentrationThe reaction mixture was concentrated
customthe product was isolated by preparative HPLC

Sources & evidence

ORD record: ord-478b246d4cff4b43a73e692e0a922f9a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426602B2

Reaction notes

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