2,4-Dichlorobenzylamine → HCID 10336950, compound

HRID 1611513Notes

Reaction equation

HRID 1611513 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12.[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].C(N(CC)C(C)C)(C)C>C(OCCO)C>[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12

Participants

5

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 81531DiisopropylethylamineHCID 118164017-Chlorothieno[3,2-b]pyridine-6-carbonitrile

Product 1

HCID 10336950HCID 10336950, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 7-chlorothieno[3,2-b]pyridine-6-carbonitrile (200 mg, 1.03 mmol), 2,4-dichlorobenzylamine (217.6 mg, 0.17 mL, 1.24 mmol), N,N-diisopropylethylamine in 5 mL of 2-ethoxyethanol is heated at reflux for 4 hours. After cooling the mixture is concentrated in vacuo and the residue is treated with a saturated aqueous sodium bicarbonate solution for 1 hour. The precipitate is collected by filtration, washed with water, dried in vacuo, and then purified by flash column chromatography eluting with a gradient of 2% methanol in dichloromethane to 4% methanol in dichloromethane to provide 261.2 mg of 7-[(2,4-dichlorobenzyl)amino]thieno[3,2-b]pyridine-6-carbonitrile as a white solid, mp 215-216° C.; 1H NMR (DMSO-d6) δ 4.95 (d, J=5 Hz, 2H), 7.28 (d, J=6 Hz, 1H), 7.40 (dd, J=6, 2 Hz, 1H), 7.46 (dd, J=4, 2 Hz, 1H), 7.69 (d, J=2 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 8.16 (m, 1H) 8.47 (d, J=6 Hz, 1H); MS 334.0, 335.8 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling the mixture
  4. concentrationis concentrated in vacuo
  5. additionthe residue is treated with a saturated aqueous sodium bicarbonate solution for 1 hour
  6. filtrationThe precipitate is collected by filtration
  7. washwashed with water
  8. customdried in vacuo
  9. custompurified by flash column chromatography
  10. washeluting with a gradient of 2% methanol in dichloromethane to 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-d098a0b9ab1b4d95a46bca96f31ff896
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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