Sodium Carbonate → 5-(5-Methyl-1H-pyrazol-4-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine

HRID 605905

Reaction equation

HRID 605905 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]4[N:17]([N:29]=[CH:30][N:31]=4)[C:18](C4C=C(C(N)=O)SC=4)=[CH:19][N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.BrC1N2N=CN=C2C(NC2C=CC(N3CCN(C)CC3)=CC=2)=NC=1.[CH3:56][C:57]1[NH:61][N:60]=[CH:59][C:58]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH3:56][C:57]1[NH:61][N:60]=[CH:59][C:58]=1[C:18]1[N:17]2[N:29]=[CH:30][N:31]=[C:16]2[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[CH:9][CH:10]=2)=[N:20][CH:19]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 177502703-Methyl-1H-pyrazole-4-boronic acid pinacol esterHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57590000(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Product 1

HCID 1359004445-(5-Methyl-1H-pyrazol-4-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amineYield 7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (132 mg, 0.340 mmol), 5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (141 mg, 0.68 mmol), Pd(PPh3)4 (98 mg, 0.085 mmol) and 1.5N Na2CO3 (1.81 mL, 2.72 mmol) in dioxane (5.4 mL). The crude product is purified by silica gel column chromatography eluting with 95:5 DCM:NH3 (7M in MeOH) followed by trituration with diethyl ether and petroleum ether to afford the title compound (9 mg, 7%) as a pale green solid. 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.27 (3H, s), 2.38-2.49 (7H, m), 3.14 (4H, m), 6.97 (2H, d), 7.70 (1H, s), 7.88 (2H, d), 7.99 and 8.43 (1H, br s), 8.68 (1H, s), 9.71 (1H, s), 12.92 and 12.98 (1H, br s).

Workup

  1. customThis compound may be prepared
  2. customThe crude product is purified by silica gel column chromatography
  3. washeluting with 95:5 DCM

Sources & evidence

ORD record
ord-b48e5e6f9dbc404d8df6c7d8af45e210
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Linked notes

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