4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 135900401, compound

HRID 605925Notes

Reaction equation

HRID 605925 reaction equation
CN1CCN(C2C=CC(NC3C4[N:17]([N:29]=[CH:30]N=4)[C:18]([C:21]4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.Br[C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:42][C:43]2[CH:44]=[CH:45][C:46]([N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[C:47]([CH2:49][OH:50])[CH:48]=2)=[N:35][CH:34]=1.CC1(C)C(C)(C)OB(C2C=NNC=2)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>[NH:17]1[CH:18]=[C:21]([C:33]2[N:38]3[N:39]=[CH:40][N:41]=[C:37]3[C:36]([NH:42][C:43]3[CH:44]=[CH:45][C:46]([N:51]4[CH2:56][CH2:55][O:54][CH2:53][CH2:52]4)=[C:47]([CH2:49][OH:50])[CH:48]=3)=[N:35][CH:34]=2)[CH:30]=[N:29]1

Participants

7

Reactant 3

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57589929HCID 57589929, compound

Product 1

HCID 135900401HCID 135900401, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

This compound may be prepared using methods as described for Compound 6, step 4 using [5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholin-4-yl-phenyl]-methanol (85 mg, 0.21 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-1H-pyrazole (81 mg, 0.42 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol) in 1.5M Na2CO3 (1.12 mL) and dioxane (2.0 mL). The reaction mixture is purified by silica gel column chromatography, eluting with 95:3 DCM:NH3 (7M in MeOH) followed by reverse phase preparative HPLC purification. The title compound is obtained as a pale brown solid (10 mg, 12%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.87 (4H, m), 3.77 (4H, m), 4.63 (2H, d), 5.12 (1H, t), 7.11 (1H, d), 7.84 (1H, d), 8.12 (1H, s), 8.21 (1H, s), 8.39 (1H, s), 8.69 (1H, s), 8.77 (1H, s), 9.78 (1H, s), 13.29 (1H, br s). LCMS: Rt 2.45 min (96.3%), m/z (APCI) 393 (M+H)+.

Workup

  1. customThis compound may be prepared
  2. customThe reaction mixture is purified by silica gel column chromatography
  3. washeluting with 95:3 DCM
  4. customNH3 (7M in MeOH) followed by reverse phase preparative HPLC purification

Sources & evidence

ORD record
ord-c3ade2df92844415bf3c82f663f5beab
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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