1-Hydroxybenzotriazole → HCID 178473397, compound

HRID 1908619Notes

Reaction equation

HRID 1908619 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C@@H:28]([NH2:35])[CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH2:23][CH2:22]1)=[O:20])[CH3:17].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH2:16]([O:18][C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:36])[C@@H:28]([NH:35][C:13]([C:4]2[CH:3]=[C:2]([OH:1])[N:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:5]=2)=[O:15])[CH2:29][CH2:30][S:31]([CH3:34])(=[O:32])=[O:33])[CH2:25][CH2:26]1)=[O:20])[CH3:17]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66920038HCID 66920038, compoundHCID 178524628HCID 178524628, compound

Product 1

HCID 178473397HCID 178473397, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 190 mg of 5-Hydroxy-1-phenyl-1H-pyrazole-3-carboxylic acid and 299 mg of 4-((S)-2-Amino-4-methanesulfonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 3 ml of DMF, 142 mg of HOBT, 178 mg of EDC and 0.2 ml DIPEA was added and the reaction mixture was stirred for 16 h at RT. Then, the solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 327 mg.

Workup

  1. customThen, the solvents were removed under reduced pressure
  2. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  3. additionThe fractions containing the product
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-bae9a1e28472471687bfc76d96c5a6b5
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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