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

HRID 1594110Notes

Reaction equation

HRID 1594110 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 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-6729936d0a48491f9dcee75d2accab8f
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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