Water → HCID 10346090, compound

HRID 746470Notes

Reaction equation

HRID 746470 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[CH:25]=[CH:24][N:23]([CH3:26])[C:18]4=[N:19][C:20]=3[O:21][CH3:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:29](Cl)(=[O:33])[C:30](Cl)=[O:31].[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.O>C(Cl)Cl>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:25]([C:29](=[O:33])[C:30]([N:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)=[O:31])=[CH:24][N:23]([CH3:26])[C:18]4=[N:19][C:20]=3[O:21][CH3:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 11959343HCID 11959343, compound

Product 1

HCID 10346090HCID 10346090, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(4-Fluoro-benzyl)-piperidin-1-yl]-(6-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone (100 mg, 0.26 mmol) in anhydrous CH2Cl2 (15 mL) was added oxalyl chloride (0.52 mL, 1.05 mmol, 2 M in CH2Cl2) at RT. The reaction mixture was stirred for 4 h. The reaction mixture was concentrated under reduced pressure. The residue was dried under vacuum for I h and dissolved in CH2Cl2 (15 mL). An excess amount of pyrrolidine (74 mg, 1.04 mmol) was added to the reaction mixture. After stirring for 1 h, the reaction mixture was treated with water. The organic layer was separated and washed with brine, dried and concentrated. The residue was purified by chromatography on silica gel eluting with CH2Cl2:MeOH (95:5) to give the desired product (70 mg) in 53% yield as a white solid. M+H+(507).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was dried under vacuum for I
  3. dissolutiondissolved in CH2Cl2 (15 mL)
  4. stirringAfter stirring for 1 h
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel eluting with CH2Cl2:MeOH (95:5)

Sources & evidence

ORD record
ord-1a8b27d6c47841daac7dc19dde9eaa24
Source dataset
uspto-grants-2008_07
Patent number
US07393851B2

Reaction notes

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