Hydrochloric Acid → HCID 178430224, compound

HRID 273081

Reaction equation

CO[CH:3](OC)[CH:4]([NH2:6])[CH3:5].[C:9](N1C=CN=C1)(N1C=CN=C1)=[S:10].C(N(CC)CC)C.[N:28]1([CH2:33][CH2:34][CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3([CH2:49][NH2:50])[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)=[CH:39][CH:38]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1.Cl>CN(C=O)C>[CH3:3][C:4]1[N:6]=[C:9]([SH:10])[N:50]([CH2:49][C:43]2([C:40]3[CH:41]=[CH:42][C:37]([O:36][CH2:35][CH2:34][CH2:33][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:38][CH:39]=3)[CH2:44][CH2:45][O:46][CH2:47][CH2:48]2)[CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Aminopropionaldehyde dimethyl acetal (0.2 g, 1.7 mmol), thiocarbonyldiimidazole (0.36 g, 2.0 mmol) and triethylamine (0.23 ml, 1.7 mmol) were stirred in DMF (2.0 ml) at ambient temperature for 30 minutes before heating to 50° C. for 18 hours. {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (540 mg, 1.7 mmol) was added and stirred at ambient temperature for 4 hours. 2M HCl (6 ml) was added, stirred at 70° C. for 18 hours, then c.HCl (1.0 ml) was added and the mixture stirred at 110° C. for 18 hours. The reaction mixture was cooled and partitioned between ethyl acetate (100 ml) and dilute aqueous sodium carbonate (50 ml). The organics were dried over Na2SO4 and concentrated in vacuo to give the title compound as a grey solid (600 mg, 84%). LRMS ESI+ m/z 416 [M+H]+.

Workup

stirringstirred at 70° C. for 18 hours
stirringthe mixture stirred at 110° C. for 18 hours
temperatureThe reaction mixture was cooled
custompartitioned between ethyl acetate (100 ml) and dilute aqueous sodium carbonate (50 ml)
dry with materialThe organics were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b796efc69428456c880e5d7cce14c0cf
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Linked notes

Loading…