Potassium Carbonate → HCID 68388399, compound

HRID 1500795Notes

Reaction equation

HRID 1500795 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[N:9]=[CH:10][C:5]2=[C:4]([C:17]2[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=2)[N:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:28][N:29]1[CH2:30][CH2:31][N:32]([C:35]2[CH:41]=[CH:40][C:38]([NH:39][C:2]3[N:7]=[C:6]4[N:8]([CH:11]5[CH2:16][CH2:15][CH2:14][CH2:13][O:12]5)[N:9]=[CH:10][C:5]4=[C:4]([C:17]4[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=4)[N:3]=3)=[CH:37][CH:36]=2)[CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 86677518N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Product 1

HCID 68388399HCID 68388399, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
200 °C

Procedure

N-(3-(6-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide (30 mg, 0.078 mmol), 4-(4-methylpiperazin-1-yl)aniline (16 mg, 0.084 mmol)) and potassium carbonate (25 mg, 0.077 mmol) were dissolved in t-butyl alcohol (5 mL) in a sealable microwave compatible reaction tube, then Pd2(dba)3 (1.5 mg, 0.002 mmol) and Xantphos (2 mg, 0.004 mmol) were added. The reaction tube was sealed and the reaction was heated under microwave irradiation (40 min, 200° C., 3 atm). The compound was purified by column chromatography. 1H NMR (400 MHz, CD3OD): δ 8.66 (s, 1H), 8.29 (s, 1H), 7.95 (d, 1H, J=7.6 Hz), 7.72 (m, 3H), 7.51 (t, 1H, J=8.4 Hz), 6.98 (m, 2H), 6.51-6.39 (m, 2H), 5.90 (d, 1H, J=8.8 Hz), 5.80 (dd, 1H, J=2.0 and 9.6 Hz), 4.06 (m, 1H), 3.79 (m, 1H), 3.15 (m, 4H), 3.02 (m, 1H), 2.62 (m, 5H), 2.34 (s, 3H), 2.12 (m, 1H), 1.94 (m, 1H), 1.83-1.70 (m, 2H); ESI-MS: 539.30 [M+H]+.

Workup

  1. customThe reaction tube was sealed
  2. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-127c3ce3f0d947579a39c69c6e349f09
Source dataset
uspto-grants-2015_12
Patent number
US09206176B2

Reaction notes

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