Ammonia → HCID 86762337, compound
Reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].CC([O:11][C:12](=[O:36])[NH:13][C@H:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][CH:25]=3)[CH:22]=2)[N:17]([C:32](=[O:34])[CH3:33])[C@@H:16]([CH3:35])[CH2:15]1)C.C(O[BH-](O[C:47](=O)[CH3:48])OC(=O)C)(=O)C.[Na+].N.[Cl:52][CH2:53]Cl>>[ClH:52].[CH3:53][CH:47]([N:13]([C@H:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][N:4]4[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]4)=[CH:28][CH:29]=3)[CH:22]=2)[N:17]([C:32](=[O:34])[CH3:33])[C@@H:16]([CH3:35])[CH2:15]1)[C:12](=[O:36])[OH:11])[CH3:48]Participants
Procedure
To 2-piperazinone (3.60 mg, 0.240 mmol, available from Alfa Aesar) was added dichloromethane (DCM) (2 mL) and 1-methylethyl[(cis)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 7) (63 mg, 0.160 mmol) and stirred under nitrogen for 35 min. Sodium triacetoxyborohydride (44.0 mg, 0.208 mmol) was added and left stirring overnight. The reactions were quenched with the addition of ammonium chloride (1 ml). The layers were separated and the aqueous reextracted with DCM (5 ml). The combined organics were washed with water (5 ml) and then reduced in vacuo to give a colourless solid which was dissolved in DCM for purification using flash chromatography. A gradient of 2.4% to 12.4% 2M methanolic ammonia in DCM was used and the appropriate fractions were reduced in vacuo to give the desired product as a colourless solid (54 mg).
Workup
- waitleft
- stirringstirring overnight
- customThe reactions were quenched with the addition of ammonium chloride (1 ml)
- customThe layers were separated
- washThe combined organics were washed with water (5 ml)
- customto give a colourless solid which
Sources & evidence
- ORD record
- ord-41372cab73bc4bf0bc1054c6bcaf4e67
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697725B2
Reaction notes
Loading…