Acetic Acid → HCID 68161673, compound

HRID 2041778Notes

Reaction equation

HRID 2041778 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@@H:7]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:6][C@H:5]1[CH2:29][CH3:30])(=[O:3])[CH3:2].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[C:37]([OH:40])(=[O:39])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:37]([OH:40])=[O:39].[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:21]=[CH:20][C:17]([CH2:18][N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:6][C@@H:5]1[CH2:29][CH3:30])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86669463HCID 86669463, compound

Product 1

HCID 68161673HCID 68161673, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[(2R,4S)-1-acetyl-2-ethyl-4-(phenylamino)-1,2,3,4-tetrahydro-6-quinolinyl]benzaldehyde (for a preparation see intermediate 92) (50 mg, 0.125 mmol), piperidine (0.019 mL, 0.188 mmol) and acetic acid (0.014 mL, 0.251 mmol) in dichloromethane (DCM) (4 mL) was stirred at room temperature under nitrogen for 30 min before being treated with sodium triacetoxyborohydride (34.6 mg, 0.163 mmol) portionwise. The resulting mixture was stirred at room temperature for 72 h then was partitioned between DCM (10 mL) and a saturated NaHCO3 aqueous solution (10 mL). The layers were separated and the organic phase was dried using a hydrophobic frit then concentrated in vacuo. Purification of the residue by MDAP (modifier: formic acid) gave (cis)-1-acetyl-2-ethyl-N-phenyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine formate salt (14.8 mg, 0.029 mmol, 23%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 72 h
  2. customthen was partitioned between DCM (10 mL)
  3. customThe layers were separated
  4. customthe organic phase was dried
  5. concentrationthen concentrated in vacuo
  6. customPurification of the residue by MDAP (modifier: formic acid)

Sources & evidence

ORD record
ord-9b58324b13d145718f9aaa12c69f04c6
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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