Chlorosuccinimide → HCID 178463170, compound

HRID 1024240Notes

Reaction equation

HRID 1024240 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:6][C:5]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:4]1)[CH3:2].[Cl:27]N1C(=O)CCC1=O>C(#N)C>[Cl:27][C:6]1[C:5](/[N:18]=[CH:19]/[C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[N:4][N:3]([CH2:1][CH3:2])[C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57619179[1-ethyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1H-pyrazol-3-yl]-(4-fluoro-benzyl)-amine

Product 1

HCID 178463170HCID 178463170, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To [1-ethyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1H-pyrazol-3-yl]-(4-fluoro-benzyl)-amine (P-0165, 10.1 mg, 0.0289 mmol, prepared as described in Example 105, Scheme 162) in acetonitrile (8.0 mL) was added N-chloro-succinimide (4.18 mg, 0.0318 mmol). The reaction was stirred at room temperature for 2 hours. The reaction was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give a white solid (P-0166, 1.1 mg). MS (ESI) [M+H+]+=382.1.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel column chromatography
  3. washeluting with 20% to 100% ethyl acetate in hexane
  4. customto give a white solid (P-0166, 1.1 mg)

Sources & evidence

ORD record
ord-b7f087c18c2c4af0818cad881d6e5acb
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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