Triethylamine → HCID 178493751, compound

HRID 2406789Notes

Reaction equation

HRID 2406789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([C@H:21]2[CH2:26][CH2:25][C@H:24]([C:27]([F:30])([F:29])[F:28])[CH2:23][CH2:22]2)=[O:20])[C:6]([C:9](O)=[O:10])=[N:7][CH:8]=1.[Cl-].[NH4+].Cl.C[N:35](C)CCCN=C=N.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([C@H:21]2[CH2:22][CH2:23][C@H:24]([C:27]([F:28])([F:29])[F:30])[CH2:25][CH2:26]2)=[O:20])[C:6]([C:9]([NH2:35])=[O:10])=[N:7][CH:8]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21899179Dimethylaminopropyl carbodiimide hydrochlorideHCID 178493765HCID 178493765, compound

Product 1

HCID 178493751HCID 178493751, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid (150 mg, 0.35 mmol, EXAMPLE 31 Step 4) and ammonium chloride (56 mg, 1.05 mmol) in dichloromethane (5 mL) were added 1-ethyl-3-((3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (100 mg, 0.52 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (53 mg, 0.35 mmol) and triethylamine (176 mg, 1.74 mmol) respectively. After being stirred at room temperature for 24 h, water was added to the mixture. The mixture was extracted with dichloromethane, and the extract was dried over sodium sulfate and concentrated in vacuo to afford an oil. The residual oil was purified by NH gel column chromatography (methanol/dichloromethane 1:30) followed by preparative high pressure liquid chromatography (prep. HPLC) (acetonitrile/0.01% aq. ammonia 96:4 to 4:96) to afford 75 mg (50%) of the title compound as an amorphous powder.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe extract was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford an oil
  5. customThe residual oil was purified by NH gel column chromatography (methanol/dichloromethane 1:30)

Sources & evidence

ORD record
ord-34319858228a4b708424c5fe8e1c738e
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Reaction notes

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