Acetic Acid → HCID 178523758, compound
Reaction equation
[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH2:5][CH2:4]1)=O.ClC1C=CC(C(F)(F)F)=CC=1C(N[C@H]1CC[C@H](C=O)CC1)=O.[NH2:44][C:45]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:46]=1[CH:47]=[CH:48][CH:49]=[N:50]2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[N:50]1[C:51]2[C:46](=[C:45]([NH:44][CH2:1][C@H:3]3[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:21])[C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=4)[CH2:5][CH2:4]3)[CH:54]=[CH:53][CH:52]=2)[CH:47]=[CH:48][CH:49]=1Participants
Conditions
- Temperature
- 140 °C
Procedure
To a solution of trans-N-(4-formyl-cyclohexyl)-3-trifluoromethyl-benzamide (prepared analogously to trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Ex. 1 step 3) from the appropriate starting compounds) (100 mg, 0.33 mmol) and 5-aminoquinoline (48 mg, 0.33 mmol) in dry 1,2-dichloroethane (2 mL) in a 2-5 mL capacity microwave tube, is added acetic acid (0.06 mL, 1.0 mmol) and sodium triacetoxyborohydride (178 mg, 0.84 mmol). The tube is sealed with a septum and the mixture is heated at 140° C. for 10 minutes in a Biotage Initiator microwave. After cooling to room temperature, the solvents are removed under reduced pressure and the residue is purified by chromatography on a pre-packed reverse phase column. [MH+428.45].
Workup
- customThe tube is sealed with a septum
- temperatureAfter cooling to room temperature
- customthe solvents are removed under reduced pressure
- customthe residue is purified by chromatography on a pre-packed reverse phase column
Sources & evidence
- ORD record
- ord-6ae6e6217bf0450495043179fc70d506
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273900B2
Reaction notes
Loading…