Triethylamine → HCID 71014162, compound

HRID 1430074Notes

Reaction equation

HRID 1430074 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[OH:22])=[O:14])[CH:4]=1)=O.[Cl-].[C:24]([C:26]1([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH2+:29][CH2:28][CH2:27]1)#[N:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClC(Cl)C>[C:24]([C:26]1([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][N:29]([CH2:1][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]([C:13]([NH:15][C@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]3[OH:22])=[O:14])[CH:4]=2)[CH2:28][CH2:27]1)#[N:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 867264674-formyl-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamideHCID 178509354HCID 178509354, compound

Product 1

HCID 71014162HCID 71014162, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-formyl-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (0.035 g, 0.117 mmol) in 0.50 mL dichloroethane was added 4-cyano-4-(pyridin-4-yl)piperidinium chloride (0.032 g, 0.141 mmol), sodium triacetoxyborohydride (0.037 g, 0.176 mmol), and triethylamine (0.016 mL, 0.117 mmol). The reaction mixture was stirred at room temperature overnight and concentrated. The resultant residue was subjected to purification via reverse phase HPLC. The isolated material was then purified via preparative TLC (7% MeOH/CH2Cl2) to afford the titled compound that gave a mass ion (ES+) of 470.2551 for M+H+.

Workup

  1. concentrationconcentrated
  2. customThe resultant residue was subjected to purification via reverse phase HPLC
  3. customThe isolated material was then purified via preparative TLC (7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d0f37e6e6ec1411da69d73d4569b93a9
Source dataset
uspto-grants-2015_01
Patent number
US08940765B2

Reaction notes

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