Benzylamine → HCID 76852922, compound

HRID 1821834Notes

Reaction equation

HRID 1821834 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.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+]>CO>[ClH:1].[CH2:13]([NH:20][CH2:11][C:9]1[NH:8][C:7]2=[C:2]([Cl:1])[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 578935647-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbaldehyde

Product 1

HCID 76852922HCID 76852922, compoundYield 122.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (102 mg, 0.565 mmol) was dissolved in methanol (2.5 mL). Benzylamine (70 μL, 0.62 mmol) was added. After 2 h, sodium borohydride (35 mg, 0.90 mmol) was added. After an additional 2 h, the reaction mixture was quenched by addition of 59% aqueous sodium bicarbonate. The reaction mixture was extracted with diethyl ether, dried (magnesium sulfate), and evaporated to dryness (124 mg, 81% crude). The crude material was dissolved in acetonitrile and treated with hydrochloric acid (0.46 mL, 1 M in diethyl ether) to give N-benzyl-N-[(7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]amine hydrochloride (107 mg, 0.347 mmol, 61%) as an off-white powder: mp 201-204° C.; 1H NMR (300 MHz, CD3OD) δ4.35 (2H, s), 4.52 (2H, s), 6.87 (1H, s), 7.45-7.60 (5H, m), 7.60 (1H, d, J=5.6 Hz), 7.94 (1H, d, J=5.6 Hz); ESI MS m/z 272 [C15H14ClN3+H]+; HPLC (H2O/CH3CN 90:10 to 0:100 over 20 min, hold for 15 min, 0.05% TFA added to solvents) >99%, tR=11.1 min.

Workup

  1. waitAfter an additional 2 h
  2. customthe reaction mixture was quenched by addition of 59% aqueous sodium bicarbonate
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated to dryness (124 mg, 81% crude)
  6. dissolutionThe crude material was dissolved in acetonitrile
  7. additiontreated with hydrochloric acid (0.46 mL, 1 M in diethyl ether)

Sources & evidence

ORD record
ord-8c0cd7dbbb43483f822a406263a64869
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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