Ammonia → HCID 71586646, compound

HRID 400487

Reaction equation

HRID 400487 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19](O)=[O:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:53][C:54]1[CH:55]=[N:56][C:57]([CH:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)=[N:58][CH:59]=1.N>CN(C=O)C.CO.O>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]([N:63]3[CH2:62][CH2:61][CH:60]([C:57]4[N:56]=[CH:55][C:54]([Cl:53])=[CH:59][N:58]=4)[CH2:65][CH2:64]3)=[O:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 824607(3,5-Diphenyl-pyrazol-1-yl)-acetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 552623575-Chloro-2-(4-piperidinyl)pyrimidine

Product 1

HCID 71586646HCID 71586646, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

28 mg (3,5-diphenyl-pyrazol-1-yl)-acetic acid was dissolved in 2 mL DMF and 26 mg DIPEA and 32 mg TBTU were added to this solution and the reaction was stirred for 5 minutes at RT. The mixture was added to 20 mg 5-chloro-2-piperidin-4-ylpyrimidine and stirred for 2 h. The reaction was cleaned by RP-chromatographie (methanol/water, 0.1% NH3) to yield 11 mg of the desired compound. Rt: 2.38 (method A), (M+H)+: 458

Workup

  1. stirringstirred for 2 h

Sources & evidence

ORD record
ord-49ba1563701549929f09c701a9524617
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Linked notes

Loading…