Ethylamine → HCID 76852920, compound

HRID 1821833Notes

Reaction equation

HRID 1821833 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]([NH2:15])[CH3:14].[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:15][CH2:13][CH3:14])[NH:8][C:7]=12

Participants

5

Reactant 3

HCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 578935647-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbaldehyde

Product 1

HCID 76852920HCID 76852920, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (75 mg, 0.42 mmol) was dissolved in methanol (3 mL). Ethylamine (0.23 mL, 2 M in tetrahydrofuran) was added. After 2 h, sodium borohydride (25 mg, 0.67 mmol) was added. After an additional 2 h, the reaction mixture was quenched by addition of 5% aqueous sodium bicarbonate. The reaction mixture was extracted with diethyl ether, dried (magnesium sulfate), and evaporated to dryness (50 mg, 52% crude). The crude material was dissolved in acetonitrile and treated with hydrochloric acid (0.24 mL, 1 M in diethyl ether) to give N-[(7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]-N-ethylamine hydrochloride (47 mg, 0.19 mmol, 42%) as an off-white powder: mp 242-245° C. dec.; 1H NMR (300 MHz, CD3OD) δ1.40 (3H, t, J=7.3 Hz), 3.24 (2H, q, J=7.3 Hz), 4.57 (2H, s), 7.09 (1H, s), 7.92 (1H, d, J=6.1 Hz), 8.1 (1H, d, J=6.1 Hz); ESI MS m/z 210 [C10H12ClN3+H]+; HPLC (H2O/CH3CN 75:25 to 0:100 over 20 min, hold for 10 min) 94.5%, tR=8.0 min.

Workup

  1. waitAfter an additional 2 h
  2. customthe reaction mixture was quenched by addition of 5% aqueous sodium bicarbonate
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated to dryness (50 mg, 52% crude)
  6. dissolutionThe crude material was dissolved in acetonitrile
  7. additiontreated with hydrochloric acid (0.24 mL, 1 M in diethyl ether)

Sources & evidence

ORD record
ord-32d2ea3243744d2e97d9282e040e1284
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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