2-Aminothiazole → HCID 10088931, compound

HRID 855543Notes

Reaction equation

N=C=N.[CH:4]1(/[CH:9]=[C:10](\[C:14]2[CH:15]=[N:16][C:17]([S:20][CH3:21])=[CH:18][CH:19]=2)/[C:11]([OH:13])=O)[CH2:8][CH2:7][CH2:6][CH2:5]1.C1C=CC2N(O)N=NC=2C=1.[S:32]1[CH:36]=[CH:35][N:34]=[C:33]1[NH2:37]>CN(C=O)C>[CH:4]1(/[CH:9]=[C:10](\[C:14]2[CH:15]=[N:16][C:17]([S:20][CH3:21])=[CH:18][CH:19]=2)/[C:11]([NH:37][C:33]2[S:32][CH:36]=[CH:35][N:34]=2)=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of PS-carbodiimide (1.08 g, loading 1.32 mmol g−1, 1.42 mmol), (E)-3-cyclopentyl-2-(6-methylsulfanylpyridin-3-yl)acrylic acid (Preparation 3, 125 mg, 475 μmol), and HOBt (128 mg, 949 μmol) in anhydrous DMF (8 mL) was stirred for 15 min at 20° C. Thiazol-2-ylamine (48 mg, 475 μmol) was added, then the mixture was stirred for 14 h at 20° C. LCMS indicated that the reaction had not gone to completion, so more thiazol-2-ylamine (95 mg, 950 μmol) was added. The mixture was stirred for an additional 64 h, before being filtered. The resin collected was washed with CH2Cl2, then the combined filtrate and washings were concentrated under reduced pressure. Column chromatography (2:11H-EtOAc) provided the title compound: RTA=3.85 min; m/z (ES+)=346.1 [M+H]+.

Workup

stirringthe mixture was stirred for 14 h at 20° C
additionwas added
stirringThe mixture was stirred for an additional 64 h
filtrationbefore being filtered
customThe resin collected
washwas washed with CH2Cl2
concentrationthe combined filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record: ord-c88cb08271c94d03b32c8bcb39ec534e
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262196B2

Reaction notes

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