1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-N-(2-oxopropyl)propanamide

HRID 1806122Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([OH:18])=O)[N:13]=2)=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.[NH2:58][CH2:59][C:60](=[O:62])[CH3:61]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([NH:58][CH2:59][C:60](=[O:62])[CH3:61])=[O:18])[N:13]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoic acid (0.800 g, 1.90 mmol), HOBT-H2O (0.437 g, 2.86 mmol), DIEA (1.36 mL, 7.80 mmol), EDCI (0.547 g, 2.86 mmol), and 1-aminopropan-2-one hydrochloride (0.834 g, 7.61 mmol) in 50 mL THF was stirred at 50° C. for 2 days. The mixture was concentrated and diluted with CH2Cl2 and washed with water, dried over sodium sulfate and concentrated to a residue that was carried on to the next step without further purification.

Workup

concentrationThe mixture was concentrated
additiondiluted with CH2Cl2
washwashed with water
dry with materialdried over sodium sulfate
concentrationconcentrated to a residue that
customwas carried on to the next step without further purification

Sources & evidence

ORD record: ord-12b8becd575e442aba3462f890a7ec88
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354540B2

Reaction notes

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