Diisopropylethylamine → HCID 58188345, compound

HRID 1845294Notes

Reaction equation

HRID 1845294 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:7]([OH:9])=O.[CH3:20][C:21]1[N:26]=[CH:25][C:24]([C@H:27]([NH2:29])[CH3:28])=[CH:23][N:22]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:7]([NH:29][C@@H:27]([C:24]1[CH:23]=[N:22][C:21]([CH3:20])=[N:26][CH:25]=1)[CH3:28])=[O:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 58188147HCID 58188147, compound

Product 1

HCID 58188345HCID 58188345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(methoxymethyl)-5-(5-methylpyridin-2-yl)benzoic acid (30 mg, 0.12 mmol) in N,N-dimethylformamide (1.5 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (40 mg, 0.29 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (100 mg, 0.26 mmol), and N,N-diisopropylethylamine (100 μL, 0.57 mmol). The reaction mixture was stirred for 16 hours at 25° C., and then purified by preparative HPLC to afford the final product.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-09de5d9dc4a9429f8a0fa0a8942208ee
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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