4-N-ethylpyridine-3,4-diamine → 2-[2,4']bithiazolyl-5'-ylmethyl-1-ethyl-1H-imidazo[4,5-c]pyridine

HRID 1988765Notes

Reaction equation

HRID 1988765 reaction equation
C[Al](C)C.[CH2:5]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14])[CH3:6].C(O[C:18](=O)[CH2:19][C:20]1[S:24][CH:23]=[N:22][C:21]=1[C:25]1[S:26][CH:27]=[CH:28][N:29]=1)C>C(Cl)Cl>[S:26]1[CH:27]=[CH:28][N:29]=[C:25]1[C:21]1[N:22]=[CH:23][S:24][C:20]=1[CH2:19][C:18]1[N:7]([CH2:5][CH3:6])[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]=1

Participants

5

Reactant 3

HCID 120363924-N-ethylpyridine-3,4-diamineHCID 16682925TrimethylaluminumHCID 68497464[2,4']Bithiazolyl-5'-yl-acetic acid ethyl ester

Product 1

HCID 223798652-[2,4']bithiazolyl-5'-ylmethyl-1-ethyl-1H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylaluminum (2M in toluene)(2.2 mL, 4.4 mmol) is added dropwise under N2 yo a solution of N4-Ethyl-pyridine-3,4-diamine (237 mg, 1.73 mmol) in DCM (5 mL). The mixture is stirred at room temperature for 1 hour. A solution of [2,4′]bithiazolyl-5′-yl-acetic acid ethyl ester (440 mg, 1.73 mmol) in DCM (2 mL) is added. The mixture is reluxed for 3 days. On cooling, the reaction is quenched with water added dropwise and DCM (40 mL) is added. The organic layer is separated and the aqueous layer is extracted with DCM (3×30 mL). The combined organic layers are dried and solvent removed. The residue is purified by PTLC (10% methanol in DCM) to give 2-[2,4′]bithiazolyl-5′-ylmethyl-1-ethyl-1H-imidazo[4,5-c]pyridine as a solid. 1H NMR (CDCl3) δ 9.05 (s, 1H0), 8.76 (s, 1H), 8.41 (d, 1H), 7.88 (d, 1H), 7.41 (d, 1H), 7.25 (d, 1H), 5.35 (s, 2H), 4.26 (q, 2H), 1.25 (t, 3H).

Workup

  1. waitThe mixture is reluxed for 3 days
  2. temperatureOn cooling
  3. customthe reaction is quenched with water
  4. additionadded dropwise
  5. additionDCM (40 mL) is added
  6. customThe organic layer is separated
  7. extractionthe aqueous layer is extracted with DCM (3×30 mL)
  8. customThe combined organic layers are dried
  9. customsolvent removed
  10. customThe residue is purified by PTLC (10% methanol in DCM)

Sources & evidence

ORD record
ord-44f39acae38b47c9bc46d44440e8a108
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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