Potassium Carbonate → HCID 67458408, compound

HRID 1853007Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[N:5]2[CH:20]=[CH:21][N:22]=[C:4]2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:48]1[CH:49]=[CH:50][N:51]2[CH2:56][CH2:55][N:54](C(OC(C)(C)C)=O)[CH2:53][C:52]=12>O1CCOCC1.C(O[Pd]OC(=O)C)(=O)C>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[N:5]4[CH:20]=[CH:21][N:22]=[C:4]4[CH:3]=[C:2]([C:50]4[N:51]5[CH2:56][CH2:55][NH:54][CH2:53][C:52]5=[N:48][CH:49]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:14][C:15]#[N:16])[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 95 °C

Procedure

To 3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropyl-propanenitrile (Preparation M; 100 mg, 0.320 mmol) in dioxane (10 mL) was added K2CO3 (88.4 mg, 0.639 mmol), diacetoxypalladium (7.18 mg, 0.0320 mmol), triphenylphosphine (16.8 mg, 0.0639 mmol) and tert-butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (107 mg, 0.480 mmol). The reaction was sealed and heated to 95° C. for 5 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to give the final product (33 mg, 26% yield). MS (apci) m/z=400.4 (M+H).

Workup

customThe reaction was sealed
temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Sources & evidence

ORD record: ord-07eb2592051242138a0fb1aaba6e20eb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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