Acetyl chloride → HCID 178437452, compound

HRID 1729445Notes

Reaction equation

HRID 1729445 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]2[N:11]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]4[NH:33][N:32]=[N:31][N:30]=4)=[CH:19][CH:18]=3)[C:12]([CH2:14][CH3:15])=[N:13][C:8]2=[C:7]([CH3:34])[CH:6]=1.[C:35](Cl)([CH3:37])=[O:36].C(N(CC)CC)C>C1COCC1>[C:35]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]2[N:11]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]4[NH:33][N:32]=[N:31][N:30]=4)=[CH:21][CH:22]=3)[C:12]([CH2:14][CH3:15])=[N:13][C:8]2=[C:7]([CH3:34])[CH:6]=1)(=[O:36])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178437453HCID 178437453, compound

Product 1

HCID 178437452HCID 178437452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-(2-aminoethyl)amino-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (20 mg) in THF (1 mL) at °C. was added AcCl (3.4 μL) and triethylamine (18 μL). After 1 h, the solvent was evaporated and the residue was purified (SiO2, 80:20:1CHCl3, MeOH, NH4OH) to give 17 mg of the title compound. 1H NMR (300 MHz, CD3OD) δ 7.63-7.45 (m, 4H), 7.18-7.04 (AB q, 4H), 6.33 (s, 1H), 5.43 (s, 2H), 3.47 (t, 2H J=5 Hz), 3.38 (t, 2H J=5 Hz), 2.86 (q, 2H, J=7.8 Hz), 2.47 (s, 3H), 1.90 (s, 3H), 1.22 (t, 3H, J=7.8 Hz).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified (SiO2, 80:20:1CHCl3, MeOH, NH4OH)

Sources & evidence

ORD record
ord-b7d6ab87be3240a4bff8e3f665175bd1
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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