Sodium t-butoxide → 1-(4-(5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)phenyl)piperazin-2-one

HRID 605971Notes

Reaction equation

HRID 605971 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[C:15]4[N:16]([N:25]=[CH:26][N:27]=4)[C:17]([C:20]4[CH:21]=[N:22][NH:23][CH:24]=4)=[CH:18][N:19]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5]OCC1.BrC1N2N=CN=C2C(NC2C=CC(N3CC[NH:48][CH2:47][C:46]3=[O:51])=CC=2)=NC=1.CC([O-])(C)C.[Na+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:22]1[CH:21]=[C:20]([C:17]2[N:16]3[N:25]=[CH:26][N:27]=[C:15]3[C:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([N:1]4[CH2:6][CH2:5][NH:48][CH2:47][C:46]4=[O:51])=[CH:8][CH:9]=3)=[N:19][CH:18]=2)[CH:24]=[N:23]1

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 57590076HCID 57590076, compoundHCID 135979614(4-Morpholin-4-ylphenyl)-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amine

Product 1

HCID 1359004491-(4-(5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)phenyl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

This compound may be prepared using methods as described for Compound 1, step 5 using 1-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-piperazin-2-one (70 mg, 0.18 mmol) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (64 mg, 0.33 mmol), Pd(PPh3)4 (21 mg, 18 μmol) and NaOtBu (70 mg, 0.72 mmol) in 2 mL of 3:1 DMF/water. The reaction mixture is concentrated under vacuum and the residue is purified by silica gel column chromatography eluting with a gradient 99:1 to 90:10 DCM:NH3 (7M in MeOH). The title compound is isolated as a pale green solid (13 mg, 19%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 3.05 (2H, m), 3.42 (2H, s), 3.62 (2H, m), 7.32 (2H, d), 8.07 (2H, d), 8.26 (1H, s), 8.39 (1H, br s), 8.67 (1H, br s), 8.81 (1H, s), 10.05 (1H, s), 13.32 (1H, br s). LCMS: Rt 6.98 min (92.4%), m/z (APCI) 376 (M+H)+.

Workup

  1. customThis compound may be prepared
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. customthe residue is purified by silica gel column chromatography
  4. washeluting with a gradient 99:1 to 90:10 DCM

Sources & evidence

ORD record
ord-71022417e77c4a10a9726c8ca1555873
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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