Triethylamine → HCID 178510099, compound

HRID 1480494Notes

Reaction equation

HRID 1480494 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]#[N:24])[CH:14]=2)=[O:10])[CH2:5][CH2:4]1.[NH:25]1[CH:29]=[C:28]([CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[N:27]=[N:26]1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCOC(C)=O>[NH:25]1[CH:29]=[C:28]([CH2:30][CH2:31][CH2:32][C:33]([NH:2][CH:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[C:15]([C:23]#[N:24])[CH:14]=3)=[O:10])[CH2:7][CH2:8]2)=[O:34])[N:27]=[N:26]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 86722710HCID 86722710, compoundHCID 178525383HCID 178525383, compound

Product 1

HCID 178510099HCID 178510099, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-Cyano-5-(trifluoromethyl)benzyl 4-aminopiperidine-1-carboxylate hydrochloride (50 mg, 0.137 mmol) and 4-(1H-1,2,3-triazol-4-yl)butanoic acid (25.6 mg, 0.165 mmol) were suspended in EtOAc (5 mL) and triethylamine (0.067 mL, 0.481 mmol) was added. After 5 mins at RT, T3P, 50% in EtOAC (0.164 mL, 0.275 mmol) was added and the mixture allowed to stir at RT for 20 hours. EtOAc (30 ml) was added and the mixture washed with a 10% solution of citric acid and a saturated solution of brine. The organics were dried over MgSO4, filtered and concentrated in vacuo. Purification via silica chromatography eluting with 0-10% MeOH/DCM gave the title compound.

Workup

  1. washthe mixture washed with a 10% solution of citric acid
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica chromatography
  6. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-ea3fcf57e35a424c93eb488b0a47bf0f
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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