1-Hydroxybenzotriazole → HCID 42638013, compound

HRID 1816180Notes

Reaction equation

HRID 1816180 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]([CH2:23][C:24]3[CH:36]=[CH:35][C:34]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27][C:26]=4[CH:25]=3)[C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:60][O:61][C:62](=[O:66])[CH2:63][CH2:64][NH2:65].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:60][O:61][C:62](=[O:66])[CH2:63][CH2:64][NH:65][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:14]([N:13]([C:10]2[S:11][CH:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH2:23][C:24]2[CH:36]=[CH:35][C:34]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][C:26]=3[CH:25]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 22496409HCID 22496409, compound

Product 1

HCID 42638013HCID 42638013, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-[[4-(4-Chlorophenyl)thiazol-2-yl]-(9H-fluoren-2-ylmethyl)amino]benzoic acid (300 mg; 0.59 mmol) was suspended in a mixture of DCM (4 mL) and DMF (4 mL). HOBt (88 mg; 0.64 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (128 mg; 0.64 mmol) were added. The mixture was stirred for 1 hour to give a clear solution. Then, β-alanine methyl ester hydrochloride (67 mg, 0.64 mmol) and DIPEA (350 μL) were added. The mixture was stirred at room temperature for 16 hours, then diluted with DCM (20 mL) and washed twice with water and once with brine. The organic phase was dried with anhydrous sodium sulphate and concentrated in vacuo to afford 310 mg (88%) of 3-{4-[[4-(4-chlorophenyl)thiazol-2-yl]-(9H-fluoren-2-ylmethyl)amino]benzoylamino}propionic acid methyl ester as a foam.

Workup

  1. customto give a clear solution
  2. stirringThe mixture was stirred at room temperature for 16 hours
  3. washwashed twice with water and once with brine
  4. dry with materialThe organic phase was dried with anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70ddb8d4b33845a08ff6e9e9daf1148b
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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