Diisopropylethylamine → HCID 86714421, compound

HRID 1750210Notes

Reaction equation

HRID 1750210 reaction equation
[S:1]1[C:5]([CH2:6][C:7]([OH:9])=O)=[CH:4][N:3]=[CH:2]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[C:34]([NH2:44])[CH:33]=1>O.C(Cl)CCl.CN(C=O)C>[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:40][CH3:41])[CH2:42][CH3:43])=[C:34]([NH:44][C:7](=[O:9])[CH2:6][C:5]2[S:1][CH:2]=[N:3][CH:4]=2)[CH:33]=1

Participants

8

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 181649HOAtHCID 3494395-Thiazoleacetic acidHCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Product 1

HCID 86714421HCID 86714421, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g of Thiazol-5-yl-acetic acid in 17 nil of dry DMF 0.48 g of HOAT, 1.61 g of EDC and 2.3 ml of DIPEA were added at 0° C. After 30 min 1.65 g of 3-Amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester were added, followed by the addition of 2 ml of DIPEA and the reaction was stirred at it for 48 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 to obtain 2.16 g (85%) of 4-(1-Ethyl-propylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester, which was used without further purification.

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

Sources & evidence

ORD record
ord-020405a5462942888d9e9ae400e6b484
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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