1-Hydroxybenzotriazole → HCID 21048633, compound

HRID 227450Notes

Reaction equation

HRID 227450 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]([OH:16])=O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.[CH2:48]([N:55]1[CH2:60][CH2:59][O:58][C@@H:57]([CH2:61][NH2:62])[CH2:56]1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C)C=O>[CH2:48]([N:55]1[CH2:60][CH2:59][O:58][C@@H:57]([CH2:61][NH:62][C:14](=[O:16])[CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])[CH2:56]1)[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27751395-Methyl-2-phenyl-4-oxazoleacetic acidHCID 6932054(S)-(4-benzylmorpholin-2-yl)methanamine

Product 1

HCID 21048633HCID 21048633, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (5-methyl-2-phenyl-oxazol-4-yl)-acetic acid (0.263 g), 1-hydroxylbenzotriazole (0.163 g), and N,N-diisopropylethylamine (0.211 ml) in N,N-dimethylformamide (3 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.232 g). The mixture was stirred for 5 min, treated with 1-[(2S)-4-benzylmorpholin-2-yl]methanamine (prepared in accordance with EP 0 995 746 A1; 0.192 g), and the solution was stirred at 22° C. for 18 h. The mixture was partitioned between dichloromethane (20 ml) and saturated aqueous sodium hydrogen carbonate (10 ml). The phases were separated in a hydrophobic frit; the organic phase was loaded onto a solid phase extraction cartridge (10 g SCX) and eluted with methanol, followed by 0.880 ammonia:methanol 10:90 to give the title compound as a colourless gum (0.394 g).

Workup

  1. stirringthe solution was stirred at 22° C. for 18 h
  2. customThe mixture was partitioned between dichloromethane (20 ml) and saturated aqueous sodium hydrogen carbonate (10 ml)
  3. customThe phases were separated in a hydrophobic frit
  4. extractionthe organic phase was loaded onto a solid phase extraction cartridge (10 g SCX)
  5. washeluted with methanol

Sources & evidence

ORD record
ord-fc4e6cc5e97e44efaf8f680d41d5184b
Source dataset
uspto-grants-2009_07
Patent number
US07560548B2

Reaction notes

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