2-Chloro-4-fluorobenzene-1-sulfonyl chloride → HCID 67220287, compound

HRID 916759Notes

Reaction equation

HRID 916759 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:15]2[C:22]([C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=3)=[O:24])=[CH:21][N:20]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:16]=2[N:17]=[CH:18][N:19]=1>N1C=CC=CC=1>[NH2:13][C:14]1[C:15]2[C:22]([C:23]([C:25]3[CH:26]=[C:27]([NH:31][S:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[Cl:1])(=[O:11])=[O:10])[CH:28]=[CH:29][CH:30]=3)=[O:24])=[CH:21][N:20]([CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[C:16]=2[N:17]=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 5228462-Chloro-4-fluorobenzene-1-sulfonyl chlorideHCID 11859044(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)methanone

Product 1

HCID 67220287HCID 67220287, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-4-fluorobenzenesulphonyl chloride (85.7 mg, 0.37 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone (80 mg, 0.25 mmol) in pyridine (3 mL). The resulting solution was heated to 120° C. for 3 h. The reaction was quenched with water and concentrated. The residue was dissolved in EtOAc and washed with 1N NaOH (1×) and water (1×). The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH 98:2) afforded the title compound as a white solid (32 mg, 25%). MS: 514.1/516.1 (MH+); HPLC Rf: 6.12 min. (HPLC method 4).

Workup

  1. customThe reaction was quenched with water
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1N NaOH (1×) and water (1×)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-6b975017af144f6b83f3374575b74833
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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