Dimethylformamide → HCID 68986687, compound

HRID 240796Notes

Reaction equation

HRID 240796 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C=O.[CH3:48][O:49][C:50]1[CH:51]=[C:52]([C@H:56]([NH2:58])[CH3:57])[CH:53]=[CH:54][CH:55]=1>O>[Br:1][C:2]1[S:3][C:4]([C:7]([NH:58][C@@H:56]([C:52]2[CH:53]=[CH:54][CH:55]=[C:50]([O:49][CH3:48])[CH:51]=2)[CH3:57])=[O:9])=[CH:5][N:6]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27632102-Bromothiazole-5-carboxylic acidHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68986687HCID 68986687, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 2-bromothiazole-5-carboxylic acid (0.3 g, 1.442 mmol), diisopropyl ethylamine (0.205 g, 1.586 mmol) and HATU (0.603 g, 1.586 mmol) in dimethylformamide (7.21 mL, 1.442 mmol) was added (R)-1-(3-methoxyphenyl)ethanamine (0.218 g, 1.442 mmol) dropwise. After stirring for 12 hours at 50° C., the reaction was poured into water (50 mL). The precipitated solid was then collected by filtration washing successively with water (2×50 mL) and hexanes (2×50 mL). The recovered product was used without further purification in the next step.

Workup

  1. filtrationThe precipitated solid was then collected by filtration
  2. washwashing successively with water (2×50 mL) and hexanes (2×50 mL)
  3. customThe recovered product was used without further purification in the next step

Sources & evidence

ORD record
ord-b0c6fca811c840bb847791ab06c467b0
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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