1-Hydroxybenzotriazole → HCID 72984654, compound

HRID 1039125Notes

Reaction equation

HRID 1039125 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]=[C:10]([C:13](=[N:15][NH:16][C:17]([N:19]3[CH2:24][CH2:23][CH:22]([C:25](O)=[O:26])[CH2:21][CH2:20]3)=[S:18])[CH3:14])[C:9]=2[OH:28])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[N:60]1[CH:65]=[CH:64][C:63]([CH2:66][NH2:67])=[CH:62][CH:61]=1>O.CN(C)C=O>[N:60]1[CH:65]=[CH:64][C:63]([CH2:66][NH:67][C:25]([CH:22]2[CH2:21][CH2:20][N:19]([C:17]([NH:16][N:15]=[C:13]([C:10]3[C:9]([OH:28])=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)[S:12][CH:11]=3)[CH3:14])=[S:18])[CH2:24][CH2:23]2)=[O:26])=[CH:62][CH:61]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 73072595HCID 73072595, compound

Product 1

HCID 72984654HCID 72984654, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To 1-{1-[5-(4-bromophenyl)-4-hydroxythiophen-3-yl]-ethylidene-hydrazinothiocarbonyl}-piperidine-4-carboxylic acid (84 mg, 0.17 mmol) prepared in Synthetic Example 9, dimethylformamide (2 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (66 mg, 0.25 mmol) and HOBt (47 mg, 0.25 mmol) were added, and then dimethylformamide (2.5 mL) and diisopropylethylamine (91 μl, 0.52 mmol) were added. The resulting solution was stirred at room temperature for 1 hour and then stirred with a dimethylformamide solution (1.5 mL) of 4-picolylamine (47 mg, 0.43 mmol) for 24 hours. After addition of water, the reaction mixture was filtered, and the filter cake was dried and washed with isopropyl alcohol repeatedly to give the desired product (yield 34%).

Workup

  1. additionwere added
  2. filtrationthe reaction mixture was filtered
  3. customthe filter cake was dried
  4. washwashed with isopropyl alcohol repeatedly

Sources & evidence

ORD record
ord-643abf52b56b4ef3bb715a2c615d7b50
Source dataset
uspto-grants-2013_10
Patent number
US08552031B2

Reaction notes

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