Triethylamine → HCID 16059694, compound

HRID 1710667Notes

Reaction equation

HRID 1710667 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][C:11]([OH:13])=O)[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.Cl.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][C:19]=1[O:31][CH3:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][C:11]([N:27]3[CH2:28][CH2:29][C:24]([C:21]4[CH:22]=[CH:23][C:18]([Cl:17])=[C:19]([O:31][CH3:32])[CH:20]=4)([OH:30])[CH2:25][CH2:26]3)=[O:13])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 776366(6-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acidHCID 68499636HCID 68499636, compound

Product 1

HCID 16059694HCID 16059694, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetic acid (22.7 mg, 0.1 mmol, 1 equiv), 4-(4-chloro-3-methoxy-phenyl)-piperidin-4-ol hydrochloride (69) (27.7 mg, 1 equiv), BOP (58 mg, 1.3 equiv), triethylamine (56 μL, 4 equiv) in 1 ml of DMF was stirred at room temperature for overnight. The solution was then diluted with EtOAc (50 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by flash chromatography to provide 6-chloro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-4-hydroxy-piperidin-1-yl]-2-oxo-ethyl}-3H-benzooxazol-2-one (70): MS (ES) [M+H]+ expected 451.1, found 451.1.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ad27e02a656b4de290f9b4f3af6574cd
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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