2-Chloroaniline → HCID 59643070, compound

HRID 2251091Notes

Reaction equation

HRID 2251091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:19](Cl)=[O:20])=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25].C(N(CC)CC)C>ClCCl.O>[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][C:19]([C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1)=[O:20]

Participants

6

Reactant 3

HCID 72402-ChloroanilineHCID 8471TriethylamineHCID 59643072HCID 59643072, compound

Product 1

HCID 59643070HCID 59643070, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(4-fluoro-phenyl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl chloride, 25, (0.57 g, 1.77 mmol) in dichloromethane (10 mL) is added 2-chloroaniline (0.28 mL, 2.66 mmol) and triethylamine (0.74 mL, 5.3 mmol). The mixture is allowed to stir at ambient temperature for 16 hours. The reaction was diluted with H2O and extracted three times with EtOAc. The combined organic phases are rinsed with brine, dried (MgSO4), filtered and concentrated in vacuo wherein the crude residue is purified over silica (5% to 40% EtOAc/hexanes) to afford 365 mg the desired product: 1H NMR (300 MHz, CDCl3) δ 9.00 (s, 1H), 8.42 (d, J=8.2 Hz, 1H), 8.32 (br s, NH), 7.55-7.50 (m, 2H), 7.42 (d, J=8.2 Hz, 1H), 7.36-7.20 (m, 3H), 7.12 (t, J=8.7 Hz, 1H), 2.49 (s, 3H); ESI+ MS: m/z (rel intensity) 413.0 (100, M++H).

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic phases are rinsed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo wherein the crude residue
  6. customis purified over silica (5% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1e1b4f4bf0014410b9e9b74cce0beea4
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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