1-Hydroxybenzotriazole → HCID 10120494, compound

HRID 1829998Notes

Reaction equation

HRID 1829998 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:25])[CH2:14][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](O)=[O:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:48][C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:56]([NH:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[CH3:65])=[O:57])=[CH:51][CH:50]=1>CC#N>[CH3:65][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=1[NH:58][C:56]([NH:55][C:52]1[CH:51]=[CH:50][C:49]([NH:48][C:16](=[O:17])[CH:15]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:14][C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)=[O:25])=[CH:54][CH:53]=1)=[O:57]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11253499HCID 11253499, compoundHCID 22056516HCID 22056516, compound

Product 1

HCID 10120494HCID 10120494, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-{[4-(Ethoxycarbonyl)phenyl]amino}-4-oxo-2-phenylbutanoic acid (400 mg, 1.17 mmol) was dissolved in MeCN (10 mL), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimidhydrochlorid (247 mg, 1.29 mmol), 1-hydroxy-1H-benzotriazol (158 mg, 1.17 mmol) followed by N-(4-aminophenyl)-N′-(2-methylphenyl)urea (282 mg, 5 1.17 mmol) was added at r.t and the reaction mixture was stirred for 24 h. Ethyl 4-[(4- {[4-({[(2-methylphenyl)amino]carbonyl} amino)phenyl]amino}-4-oxo-3-phenyl-butanoyl)amino]benzoate (194 mg, 0.34 mmol) was isolated by filtration as a colorless solid. M.p.>220° C.; TLC (DCM/MeOH 9/1) Rf 0.21; 1H NMR (400 MHz, D6-DMSO) δ 1.30 (t, J=7.1 Hz, 3H); 2.23 (s, 3H); 2.80 (mc, 1H); 3.25 (mc, 1H); 4.25–4.30 (m, 3H); 3.74 (s, 3H); 6.00 (bs, 1H); 6.65 (d, J=6.6 Hz, 2H); 6.90–6.96 (m, 2H); 7.10–7.19 (m, 4H); 7.34–7.38 (m, 2H); 7.43–7.51 (m, 2H); 7.69–7.71 (m, 1H); 7.79–7.90 (m, 2H); 8.70 (s, 1H); 8.97 (s, 1H).

Workup

  1. additionwas added at r.t

Sources & evidence

ORD record
ord-dc3b167e136a45a882c1532a14182fa8
Source dataset
uspto-grants-2006_06
Patent number
US07064229B2

Reaction notes

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