Potassium Carbonate → HCID 68905909, compound

HRID 729523Notes

Reaction equation

[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(#N)C.C(Cl)Cl>[O:41]([CH2:40][CH2:39][N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH3:25])[CH:18]=2)[N:9]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 100 mg (0.24 mmol) {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine and 70 mg (0.48 mmol) potassium carbonate in 5 mL acetonitrile was treated with 0.074 mL (0.48 mmol) β-bromophenetole at 0° C. The mixture was stirred at 50° C. for 8 h before it was cooled to ambient temperature for 16 h at which time MS showed that all starting materials had converted to product. The reaction mixture was diluted with 50 mL DCM, washed with 50 mL satd. NaHCO3, and dried over anhydrous Na2SO4. After purification by chromotography, the title compound was obtained.

Workup

temperaturewas cooled to ambient temperature for 16 h at which time MS
washwashed with 50 mL
dry with materialNaHCO3, and dried over anhydrous Na2SO4
customAfter purification by chromotography

Sources & evidence

ORD record: ord-204ee11021b2488bbe980514061e3cec
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582631B2

Reaction notes

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