Triethylamine → HCID 60205519, compound

HRID 875816Notes

Reaction equation

HRID 875816 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:10]([F:19])=[C:11]2[C:17]([NH2:18])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1.C[C:21]1([C:24]([OH:26])=O)[CH2:23][CH2:22]1.[O:27]=[C:28]1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[Br:8][C:9]1[C:10]([F:19])=[C:11]2[C:17]([NH:18][C:24]([C:21]3([O:27][CH3:28])[CH2:23][CH2:22]3)=[O:26])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 813261-Methylcyclopropanecarboxylic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205519HCID 60205519, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (550 mg, 0.757 mL, 5.43 mmol) was slowly added to a mixture of 5-bromo-4-fluoro-1H-indol-3-amine (250 mg, 1.087 mmol, Example 1, step H), 1-methylcyclopropanecarboxylic acid (151 mg, 1.30 mmol) and bis(2-oxooxazolidin-3-yl)phosphinic chloride (415 mg, 1.63 mmol) in anhydrous dichloromethane (10 mL). The resulting solution was stirred at room temperature for 3 hours. The mixture was concentrated, and the residue purified by reverse phase chromatography (Biotage SP4 C-18 25M column, 10-75% CH3CN/water, 25CV) to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methoxycyclopropanecarboxamide (216.5 mg, 60%) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.04 (br s, 1H), 9.57 (s, 1H), 8.36 (d, 1H), 7.54 (d, 1H), 3.39 (s, 3H), 1.16-1.11 (m, 4H). LCMS (APCI+) m/z 327.9 (M+H)+, Retention time=2.96 minutes.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by reverse phase chromatography (Biotage SP4 C-18 25M column, 10-75% CH3CN/water, 25CV)

Sources & evidence

ORD record
ord-61c78bbcbed849df92cbfeb2c7847562
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

Loading…