Diisopropylethylamine → HCID 24820917, compound

HRID 552544Notes

Reaction equation

HRID 552544 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]([OH:18])=O)N=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:19][O:20][C:21]([C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1)=[O:22].[CH2:29](N(C(C)C)C(C)C)C>CC(N(C)C)=O.C(Cl)Cl>[CH3:19][O:20][C:21]([C:23]1[N:24]=[C:25]([NH:28][C:16]([C:11]2[CH:29]=[C:9]([C:4]3[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=3)[CH:14]=[C:13]([CH3:15])[N:12]=2)=[O:18])[S:26][CH:27]=1)=[O:22]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 67165198HCID 67165198, compound

Product 1

HCID 24820917HCID 24820917, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 100 mg (0.40 mmol) of 4-(3,5-Difluorophenyl)-6-methyl-pyrimidine-2-carboxylic acid, and 2-Amino-thiazole-4-carboxylic acid methyl ester in 5 ml of dry Dimethylacetamide were added 0.34 ml N-Ethyldiisopropylamine and 141.7 mg (0.44 mmol) of o-(Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU). After stirring overnight at room temperature, the mixture was diluted with 15 ml of methylene chloride, and worked up according to standard procedures. The crude material was purified by flash chromatography on silicagel using an Ethyl acetate/Heptane 1:4 mixture as eluant to yield the title compound as a light yellow crystalline solid, MS (ISP): m/e=390.2 (M+H)+.

Workup

  1. customThe crude material was purified by flash chromatography on silicagel

Sources & evidence

ORD record
ord-b1b9c9ff4baf44b9a2292d9ab1101ef5
Source dataset
uspto-grants-2011_05
Patent number
US07951824B2

Reaction notes

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