1-Hydroxybenzotriazole → HCID 86714418, compound

HRID 1750207

Reaction equation

HRID 1750207 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:30][O:31][C:32](=[O:46])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[C:35]([NH2:45])[CH:34]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:30][O:31][C:32](=[O:46])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH:40]([CH2:41][CH3:42])[CH2:43][CH3:44])=[C:35]([NH:45][C:8](=[O:10])[CH2:7][C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:34]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 44267162-(5-chlorothiophen-2-yl)acetic AcidHCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Product 1

HCID 86714418HCID 86714418, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g of 5-Chlorothiophen-2-yl-acetic acid in 15 ml of dry DMF 0.84 g of HOBT, 1.19 g of EDC and 1.5 ml of DIPEA were added at 0° C. After 30 min 1.33 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 1.5 ml of DIPEA were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by crystallization from diethylether to yield 2.00 g (89%) of 3-[2-(5-Chloro-thiophen-2-yl)-acetylamino]-4-(1-ethyl-propylamino)-benzoic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by crystallization from diethylether

Sources & evidence

ORD record
ord-bd67a932963d4c55a2a26753a700da1d
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Linked notes

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