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

HRID 335196

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-fa236ce5a76348cc90fe3f84b196a196
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883828B2

Linked notes

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