1-Hydroxybenzotriazole → HCID 46940550, compound

HRID 455012

Reaction equation

HRID 455012 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[NH:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([C:20]([OH:22])=O)[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:34]=[CH:33][C:28]2[NH:29][C:30](=[O:32])[O:31][C:27]=2[CH:26]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[O:32]=[C:30]1[NH:29][C:28]2[CH:33]=[CH:34][C:25]([NH:24][C:20]([C:18]3[CH:17]=[CH:16][C:14]4[N:15]=[C:11]([NH:10][C:9]([NH:8][C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[O:23])[S:12][C:13]=4[CH:19]=3)=[O:22])=[CH:26][C:27]=2[O:31]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86661381HCID 86661381, compound

Product 1

HCID 46940550HCID 46940550, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Starting material 35 (300 mg, 45% content, 0.4 mmol) and 6-Amino-3H-benzooxazol-2-one (30, 58 mg, 0.4 mmol) were dissolved in 2 ml of dry DMF. Then EDCl (96 mg, 0.5 mmol) and HOBt (76 mg, 0.5 mmol) were added. The reaction was stirred at ambient temperature over night. It was then purred into water and the resulting precipitate was filtered. The isolated precipitate was then stirred in 100 ml warm methanol and the non-soluble crystals filtered and washed with methanol. Thereby the desired product 36 (130 mg, 0.271 mmol, 70%) could be isolated.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. stirringThe isolated precipitate was then stirred in 100 ml
  3. temperaturewarm methanol
  4. filtrationthe non-soluble crystals filtered
  5. washwashed with methanol

Sources & evidence

ORD record
ord-d1ab1390220a4213af605416c18756cd
Source dataset
uspto-grants-2013_07
Patent number
US08497283B2

Linked notes

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