Triethylamine → HCID 69063874, compound

HRID 2116696Notes

Reaction equation

HRID 2116696 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[C:17]=1[OH:18])[CH2:5][C@@H:6]([CH2:11][C:12]([O-:14])=O)[C:7]([O:9][CH3:10])=[O:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[NH:52]1[CH2:57][CH2:56][CH:55]([N:58]2[CH2:64][CH2:63][C:62]3[CH:65]=[CH:66][CH:67]=[CH:68][C:61]=3[NH:60][C:59]2=[O:69])[CH2:54][CH2:53]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[C:17]=1[OH:18])[CH2:5][C@@H:6]([CH2:11][C:12](=[O:14])[N:52]1[CH2:53][CH2:54][CH:55]([N:58]2[CH2:64][CH2:63][C:62]3[CH:65]=[CH:66][CH:67]=[CH:68][C:61]=3[NH:60][C:59]2=[O:69])[CH2:56][CH2:57]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 86615580HCID 86615580, compound

Product 1

HCID 69063874HCID 69063874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.19 g (4.9 mmol) 1-methyl (S)-2-(3-chloro-4-hydroxy-5-trifluoromethyl-benzyl)-succinate, 1.56 g (4.9 mmol) TBTU, 0.73 ml (5.0 mmol) triethylamine, 1.65 g (4.8 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one and 30 ml DMF was stirred for 12 hours at RT. The reaction mixture was evaporated down under reduced pressure, the residue was taken up in 200 ml EtOAc and washed with 200 ml 10% citric acid solution and 50 ml saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried and evaporated down under reduced pressure.

Workup

  1. customThe reaction mixture was evaporated down under reduced pressure
  2. washwashed with 200 ml 10% citric acid solution and 50 ml saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic phase was dried
  4. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-68dbf4f385984faeaf2e2ede166e0710
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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