Potassium Carbonate → HCID 68906135, compound

HRID 729524Notes

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:32](=O)([O-])[O-].[K+].[K+].[O:38]([CH2:45][CH2:46]CBr)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(#N)C.C(Cl)Cl>[O:38]([CH:45]([CH3:46])[CH2:32][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:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 50 mg (0.12 mmol) {4-[5-(2,5-diaza-bicyclo[2.2. I]hept-2-yl)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine and 30 mg (0.24 mmol) potassium carbonate in 2 mL acetonitrile was treated with 0.040 mL (0.24 mmol) 3-phenoxy-propyl bromide at 0° C. The mixture was stirred at 50° C. for 16 h at which time MS showed that all starting materials had converted to product. The reaction mixture was cooled to ambient temperature, diluted with 50 mL DCM, washed with 50 mL satd. NaHCO3, and dried over anhydrous Na2SO4. After purification by BPLC, the title compound was obtained. MS (ES+): 546 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
washwashed with 50 mL
dry with materialNaHCO3, and dried over anhydrous Na2SO4
customAfter purification by BPLC

Sources & evidence

ORD record: ord-53e4f94d2ed44077aeff622cbab76647
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582631B2

Reaction notes

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