Triethylamine → HCID 67299326, compound

HRID 1958678Notes

Reaction equation

HRID 1958678 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[C:25]1([C:31]2([C:37]([NH2:39])=[O:38])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([N:34]2[CH2:33][CH2:32][C:31]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:37]([NH2:39])=[O:38])[CH2:36][CH2:35]2)=[O:16])=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30171304-Phenylpiperidine-4-carboxamideHCID 67185778HCID 67185778, compound

Product 1

HCID 67299326HCID 67299326, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g of the compound obtained in stage 1E), 1.27 g of 4-phenylpiperidine-4-carboxamide (Preparation 2), 2.22 ml of Et3N and 1.86 g of TBTU are added to 40 ml of CH2Cl2. The mixture is stirred at AT for 3 hours. It is evaporated to dryness, water is added and extraction is carried out with ethyl acetate. The organic phase is dried and then evaporated. After purifying by chromatography on silica (eluent: heptane-AcOEt (gradient from 0% to 30%)), 2.8 g of the expected compound are obtained.

Workup

  1. customIt is evaporated to dryness, water
  2. additionis added
  3. extractionextraction
  4. customThe organic phase is dried
  5. customevaporated
  6. customAfter purifying by chromatography on silica (eluent: heptane-AcOEt (gradient from 0% to 30%)), 2.8 g of the expected compound
  7. customare obtained

Sources & evidence

ORD record
ord-4baf42ecca6a41039dd8a6ea48ea5c35
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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