Acetyl chloride → HCID 67499722, compound

HRID 1191635Notes

Reaction equation

HRID 1191635 reaction equation
[Cl:1][C:2]1[N:3]([NH2:13])[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[Cl:1][C:2]1[N:3]([NH:13][C:21](=[O:23])[CH3:22])[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67500002HCID 67500002, compound

Product 1

HCID 67499722HCID 67499722, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-Chloro-4-(pyridin-3-yl)-1H-imidazol-1-amine (30 mg, 0.15 mmol) and triethylamine (15 mg, 0.15 mmol) in dichloromethane (5 mL) was added acetyl chloride (12 mg, 0.15 mmol) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C. The solvent was removed in vacuum and the residue was purified by prep-TLC (petroleum ether:ethyl acetate=1:2) to give the title compound (10 mg, 27%) as a yellow solid: mp 129-131° C.; 1H NMR (300 MHz, CDCl3) δ 10.69 (br, 1H), 8.81-8.80 (m, 1H), 8.44-8.43 (m, 1H), 8.02-8.00 (m, 1H), 7.33 (br s, 2H), 2.20 (s, 3H); ESIMS m/z 237 [(M+H)]+.

Workup

  1. customThe solvent was removed in vacuum
  2. customthe residue was purified by prep-TLC (petroleum ether:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-342682ec4db640fb96f15824fc5b3771
Source dataset
uspto-grants-2014_03
Patent number
US08680121B2

Reaction notes

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