Triethylamine → HCID 86758718, compound

HRID 2301174Notes

Reaction equation

HRID 2301174 reaction equation
[CH:1]([C@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][N:5]([C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:4]1)=O.Cl.Cl.[CH2:34]([N:37]([CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)[C:38]1[N:43]=[CH:42][CH:41]=[CH:40][N:39]=1)[CH:35]=[CH2:36].C(N(CC)CC)C>ClCCl.CCOC(C)=O>[CH2:34]([N:37]([CH:44]1[CH2:49][CH2:48][N:47]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=3)[CH2:6][N:5]([C@@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]3[CH2:21][C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:4]2)[CH2:46][CH2:45]1)[C:38]1[N:43]=[CH:42][CH:41]=[CH:40][N:39]=1)[CH:35]=[CH2:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18374758HCID 18374758, compoundHCID 131723726HCID 131723726, compound

Product 1

HCID 86758718HCID 86758718, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 2-(R)-(3-(S)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-cyclohexaneacetic acid, benzyl ester 83 mg, 0.195 mmol; prepared above as Aldehyde 6), 4-(N-allyl-N-(pyrimid-2-yl)-amino)piperidine dihydrochloride (64 mg, 0.219mmol, from Step A), 104 mg (0.49 mmol) NaHB(OAc)3, and 0.035 ml (0.25 mmol) triethylamine 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 83 mg of the title compound. RF: 0.3 (5% EtOAc/hexane). 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: 4.6 minutes.

Workup

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

Sources & evidence

ORD record
ord-f64ed0f98f40488c84b04447ee660336
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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