Ethylamine → Brd4-IN-8

HRID 930846Notes

Reaction equation

HRID 930846 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](Cl)=[O:12])[C:5]2[CH:24]=[CH:25][NH:26][C:4]=2[C:3]1=[O:27].[CH2:28]([NH2:30])[CH3:29]>O1CCCC1>[CH2:28]([NH:30][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([C:6]2[C:5]3[CH:24]=[CH:25][NH:26][C:4]=3[C:3](=[O:27])[N:2]([CH3:1])[CH:7]=2)[CH:9]=1)[CH3:29]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 896572813-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzoyl chloride

Product 1

HCID 71616418Brd4-IN-8Yield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 13a (0.040 g, 0.11 mmol) in tetrahydrofuran (1 mL) was treated with ethylamine (0.21 mL of a 2 M solution in tetrahydrofuran, 0.42 mmol) for 2 h. The reaction mixture was concentrated and the residue purified by preparative HPLC (C18, 10-90% acetonitrile in 0.1% TFA in water) to afford the title compound (0.025 g, 61%). 1H NMR (500 MHz, DMSO-d6) δ 1.12 (t, J=7.32 Hz, 3H), 3.25-3.32 (m, 2H), 3.54 (s, 3H), 6.23-6.24 (m, 1H), 6.95-6.99 (m, 3H), 7.11 (t, J=7.48 Hz, 1H), 7.27 (t, J=2.75 Hz, 1H), 7.31-7.37 (m, 3H), 7.84 (dd, J=8.54, 2.44 Hz, 1H), 7.98 (d, J=2.44 Hz, 1H), 8.46 (t, J=5.49 Hz, 1H), 11.99 (s, 1H). MS (ESI+) m/z 388.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by preparative HPLC (C18, 10-90% acetonitrile in 0.1% TFA in water)

Sources & evidence

ORD record
ord-77b2a8e0e0e6429480b6e2a6b734b04c
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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