2,6-Difluorobenzoyl chloride → HCID 67219785, compound

HRID 916761Notes

Reaction equation

HRID 916761 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=3)=[O:23])=[CH:20][N:19]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[C:15]=2[N:16]=[CH:17][N:18]=1>N1C=CC=CC=1>[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:25]=[C:26]([NH:30][C:4](=[O:5])[C:3]4[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=4[F:11])[CH:27]=[CH:28][CH:29]=3)=[O:23])=[CH:20][N:19]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 874382,6-Difluorobenzoyl chlorideHCID 11859044(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)methanone

Product 1

HCID 67219785HCID 67219785, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

2,6-difluorobenzoyl chloride (82.1 mg, 0.47 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone (100 mg, 0.31 mol) in pyridine (3 mL). The resulting solution was heated to 120° C. for 1 h at this time the reaction was quenched with water and concentrated. The residue was dissolved in EtOAc and washed with 1N NaOH and water. The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH 97:3) afforded the title compound as a white solid (105 mg, 73%). MS: 462.2 (MH+); HPLC Rf: 5.70 min. (HPLC method 4).

Workup

  1. customwas quenched with water
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1N NaOH and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-2458bdd5da5e4447ba8f55134e48cddd
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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