1-Hydroxybenzotriazole → HCID 178440338, compound

HRID 1162858Notes

Reaction equation

HRID 1162858 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:9]([OH:10])=[C:8]([CH2:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[C:7]([CH:21]([CH3:23])[CH3:22])=[N:6]1)#[N:2].Cl.N[C@H:26]([C:28]([NH2:30])=[O:29])[CH3:27].C([N:34](CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:28]([CH2:26][CH2:27][NH:34][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12]([CH2:11][C:8]2[C:7]([CH:21]([CH3:23])[CH3:22])=[N:6][N:5]([CH2:4][CH2:3][C:1]#[N:2])[C:9]=2[OH:10])=[CH:20][CH:19]=1)(=[O:29])[NH2:30]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 178440339HCID 178440339, compound

Product 1

HCID 178440338HCID 178440338, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg of compound 46 and 145 mg of □-alaninamide hydrochloride are introduced into 10 ml of dichloromethane, and 0.8 ml of N,N-diisopropylethylamine, 215 mg of 1-hydroxybenzotriazole and 306 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride are added. The solution is stirred for 12 h. The solution is concentrated and the crude product is purified by chromatography on silica gel (dichloromethane/methanol/glacial acetic acid 100:0:5→100:10:5). 440 mg of the desired compound 47 are obtained. C20H25N5O3 (383.5); MS (ESI+): 384.2 (M+H)+, tR=3.58 min (Gradient 3).

Workup

  1. additionare added
  2. concentrationThe solution is concentrated
  3. customthe crude product is purified by chromatography on silica gel (dichloromethane/methanol/glacial acetic acid 100:0:5→100:10:5)

Sources & evidence

ORD record
ord-44efb37126b64e7e915ad91c0ad0570e
Source dataset
uspto-grants-2010_10
Patent number
US07820804B2

Reaction notes

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