(4-Chlorophenyl)acetic acid → 2-(4-chlorophenyl)-N-(5-{[7-fluoro-1-(1-hydroxypropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-3-yl)acetamide

HRID 1753005Notes

Reaction equation

HRID 1753005 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[C:18]([F:19])[C:13]=3[N:12]([CH:20]([CH3:23])[CH2:21][OH:22])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1.CCOC(C)=O>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH:1][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([C:8]([C:10]3[C:14]4[CH:15]=[N:16][CH:17]=[C:18]([F:19])[C:13]=4[N:12]([CH:20]([CH3:23])[CH2:21][OH:22])[CH:11]=3)=[O:9])[CH:3]=2)=[O:33])=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 15880(4-Chlorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90093760HCID 90093760, compound

Product 1

HCID 1183412192-(4-chlorophenyl)-N-(5-{[7-fluoro-1-(1-hydroxypropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-3-yl)acetamideYield 37.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (5-aminopyridin-3-yl)[7-fluoro-1-(2-hydroxy-1-methylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Enantiomer 2, Preparation 26, 50 mg, 0.159 mmol) and 4-chlorophenylacetic acid (27.2 mg, 0.159 mmol) in pyridine (1 mL) was added HATU (121 mg, 0.31 mmol) and the reaction was stirred at room temperature for 16 hours. The reaction was diluted with EtOAc, washed with saturated aqueous NaHCO3 solution, brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using preparative TLC eluting with 7% MeOH in DCM to afford the title compound (28 mg).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution, brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with 7% MeOH in DCM

Sources & evidence

ORD record
ord-4ac2d329602a4f0b83496376f1cfca66
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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