1-Hydroxybenzotriazole → HCID 74382644, compound

HRID 1157188Notes

Reaction equation

HRID 1157188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([OH:20])=O)[CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[N:46][C:45]=1[C:50]1[CH:55]=[CH:54][C:53]([N:56]2[CH2:61][CH:60]3[CH2:62][CH:57]2[CH2:58][NH:59]3)=[CH:52][CH:51]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:16][CH2:15][N:14]([CH2:17][C:18](=[O:20])[N:59]3[CH2:58][CH:57]4[CH2:62][CH:60]3[CH2:61][N:56]4[C:53]3[CH:54]=[CH:55][C:50]([C:45]4[N:44]=[CH:49][CH:48]=[CH:47][N:46]=4)=[CH:51][CH:52]=3)[CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68425024HCID 68425024, compoundHCID 68425214HCID 68425214, compound

Product 1

HCID 74382644HCID 74382644, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of [3-(3-Chloro-4-hydroxy-phenylcarbamoyl)-pyrrolidin-1-yl]-acetic acid (10 mg, 0.034 mmol) and HOBt (6.8 mg, 0.050 mmol) in DMF (0.5 ml) at 0° C. was added EDCl (9.6 mg, 0.050 mmol). The formed reaction mixture was stirred at 0° C. for 0.5 hour and then 2-(4-Pyrimidin-2-yl-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane hydrochloride salt (12.6 mg, 0.05 mmol) was added. After stirred at RT for overnight, the reaction mixture was purified using a Prep-HPLC to give titled compound (3.4 mg, 19% yield). Mass Spec ES (533.1, M+H)

Workup

  1. customThe formed reaction mixture
  2. stirringAfter stirred at RT for overnight
  3. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-b6bea909d23d4790bab72a9371060399
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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