Cyclopentylamine → HCID 76852923, compound

HRID 1821835Notes

Reaction equation

HRID 1821835 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]=O)[NH:8][C:7]=12.[CH:13]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14]1.[BH4-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH2:11][NH:18][CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[NH:8][C:7]=12

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 4311764Sodium borohydrideHCID 578935647-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbaldehyde

Product 1

HCID 76852923HCID 76852923, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (75 mg, 0.42 mmol) and cyclopentylamine (45 μL, 0.46 mmol) were dissolved in methanol (3 mL). After 4 h, sodium borohydride (25 mg, 0.67 mmol) was added in one portion. After an additional 2 h, the reaction mixture was quenched by addition of 2 N aqueous sodium hydroxide and extracted with diethyl ether. The organic layer was dried over sodium sulfate and evaporated. The residue was dissolved in acetonitrile and salted with 1 N ethereal hydrochloric acid. The precipitate was collected by filtration and crystallized from acetonitrile to give N-[(7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]-N-cyclopentylamine hydrochloride (35 mg, 30%) as a white solid: mp 241-244° C.; 1H NMR (300 M-z, CD3OD) δ1.70-1.95 (6H, m), 2.25 (2H, m), 3.75 (1H, m), 4.57 (2H, s), 7.09 (1H, s), 7.93 (1H, d, J=6.0 Hz), 8.12 (1H, J=6.0 Hz); ESI MS m/z 250 [C13H16ClN3+H]+; HPLC (Method C) >99% (AUC), tR=12.9 min.

Workup

  1. waitAfter an additional 2 h
  2. customthe reaction mixture was quenched by addition of 2 N aqueous sodium hydroxide
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. dissolutionThe residue was dissolved in acetonitrile
  7. filtrationThe precipitate was collected by filtration
  8. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-584248b1acd74119b62d74b5a5a4034d
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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