4-Fluorobenzoyl chloride → HCID 16064353, compound

HRID 1991125Notes

Reaction equation

HRID 1991125 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH:16]=[C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([NH2:26])[CH:24]=3)[NH:19][CH:18]=2)[CH:14]=[N:13]1>N1C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:26][C:23]2[CH:24]=[C:25]3[C:17]([C:15]4[CH:14]=[N:13][N:12]([CH3:11])[CH:16]=4)=[CH:18][NH:19][C:20]3=[N:21][CH:22]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 591286573-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine

Product 1

HCID 16064353HCID 16064353, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Fluorobenzoyl chloride (100 μL, 0.84 mmol) was added to a solution of 54 (20.0 mg, 93.7 μmol) in pyridine (2 mL). The mixture was stirred at r.t. overnight, concentrated and separated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 55 (3.99 mg, 13%). 1H NMR (400 MHz; DMSO-d6) δ 3.87 (s, 3H), 7.38 (t, J=8.8 Hz, 2H), 7.66 (s, 1H), 7.75 (s, 1H), 8.00 (s, 1H), 8.08 (dd, J=8.7, 5.4 Hz, 2H), 8.48 (dd, J=7.0, 2.2 Hz, 2H); MS (ES) m/z 377 (MH++MeCN).

Workup

  1. concentrationconcentrated
  2. customseparated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-8118176bd97d45598cfe3a4fd6c35b7c
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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