Triethylamine → HCID 18342549, compound

HRID 2301179Notes

Reaction equation

HRID 2301179 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][C:21]([O:23]CC2C=CC=CC=2)=[O:22])[CH2:4]1)=O.Cl.[CH2:32]([N:35]([CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1)[CH:33]=[CH2:34].C(N(CC)CC)C>ClCCl.CCOC(C)=O>[CH2:32]([N:35]([CH:42]1[CH2:47][CH2:46][N:45]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][N:5]([C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]3[CH2:20][C:21]([OH:23])=[O:22])[CH2:4]2)[CH2:44][CH2:43]1)[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1)[CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18374674HCID 18374674, compoundHCID 86758721HCID 86758721, compound

Product 1

HCID 18342549HCID 18342549, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared using 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, benzyl ester using (75 mg, 0.185 mmol; prepared above as Aldehyde 4), 4-(N-allyl-N-(pyrimid-2-yl)amino)piperidine hydrochloride (61 mg, 0.24 mmol) from Example 2, Step A, NaHB(OAc)3, (97 mg, 0.46 mmol) and triethylamine (0.026 ml, 0.24 mmol) in 3 ml dichloromethane. The mixture was stirred overnight at room temperature. The reaction was diluted with 100 ml EtOAc and washed with 1M NaOH and saturated NaCl. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The material was purified using flash chromatography (5% EtOAc in hexane) to provide 80 mg (71%) of the title compound. HPLC (Zorbax SB-C8 column, 4.6 mm×7.5 cm, Gradient: 90 H2O:10 CH3CN to 0 H2O:100 CH3CN over 7.5 minutes then hold at 100 CH3CN:0 H2O for 45 seconds, 2.25 mL/min, 220 nm): Retention Time: 4.4 minutes.

Workup

  1. customThe title compound was prepared
  2. washwashed with 1M NaOH and saturated NaCl
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified

Sources & evidence

ORD record
ord-83cae03f1150441aad5e17af0a1614be
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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