Triethylamine → HCID 15408846, compound

HRID 362550Notes

Reaction equation

HRID 362550 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10](C)[CH2:9]1)C1C=CC=CC=1.FC1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]([OH:29])=O)=CC=1.C1C=CC2N(O)N=[N:36]C=2C=1.CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[NH2:36][CH:11]1[CH2:12][CH2:13][N:8]([C:27](=[O:29])[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 684484-Fluoro-1-naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 5609651-Benzyl-3-methyl-4-piperidone

Product 1

HCID 15408846HCID 15408846, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 4 (Ar2 =3,4-dichlorophenyl) (200 mg, 0.433 mmol) in CH2Cl2 (5 mL) were sequentially added 4-fluoro-1-naphthoic acid (84.8 mg, 0.433 mmol), HOBT (58.5 mg, 0.434 mmol), Et3N (0.634 mL, 0.455 mmol) and DEC (85 mg, 0.434 mmol) at RT. The reaction was stirred at RT under N2 overnight. After completion the reaction was diluted with EtOAc (150 mL) and washed with brine (50 mL, 3×), dried over MgSO4, filtered and concentrated to give a crude product 5 (Ar2 =3,4-dichlorophenyl, Ar1 =4-fluoro-1-naphthyl) which was purified by flash chromatography (50 g flash grade silica gel), eluting with 4% sat'd NH3 --MeOH in CH2Cl2 to give pure compound 5 Fab Mass [M+1]+ 35 Cl 633.2, m.p. 78°-81° C.

Workup

  1. customat RT
  2. washwashed with brine (50 mL, 3×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c636cac363644e1cb1fa516978c7837d
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

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