Benzoyl chloride → HCID 57881428, compound

HRID 1962819Notes

Reaction equation

HRID 1962819 reaction equation
[NH2:1][CH2:2][C:3]1([CH:8]([N:12]2[CH:16]=[C:15]([C:17]3[C:18]4[CH:25]=[CH:24][NH:23][C:19]=4[N:20]=[CH:21][N:22]=3)[CH:14]=[N:13]2)[CH2:9][C:10]#[N:11])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:10]([CH2:9][CH:8]([C:3]1([CH2:2][NH:1][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)[N:12]1[CH:16]=[C:15]([C:17]2[C:18]3[CH:25]=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH:14]=[N:13]1)#[N:11]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 66597916HCID 66597916, compound

Product 1

HCID 57881428HCID 57881428, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(aminomethyl)cyclopentyl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (31 mg, 0.060 mmol) and benzoyl chloride (7.0 μL, 0.060 mol) in DCM (1.0 mL), was added TEA (17 μL, 0.12 mmol). After 15 minutes, the solvent was removed in vacuo and the mixture was purified via preparative-HPLC/MS (C18 eluting first with a gradient of H2O and ACN containing 0.1% TFA, followed by chromatographic purification, eluting with a gradient of H2O and ACN containing 0.15% NH4OH) to afford the product (7 mg, 27%).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe mixture was purified via preparative-HPLC/MS (C18 eluting first with a gradient of H2O and ACN containing 0.1% TFA
  3. customfollowed by chromatographic purification
  4. washeluting with a gradient of H2O and ACN containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-9fb9fc7aa06e4a3f9438b00cffc19a90
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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