3-Chlorobenzaldehyde → HCID 74763778, compound

HRID 1054321Notes

Reaction equation

HRID 1054321 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:30]([CH:32]([CH3:34])[CH3:33])#[C-:31]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:31]([NH:30][CH:32]([CH3:34])[CH3:33])=[C:13]([C:12]3[CH:15]=[CH:16][CH:17]=[C:10]([Cl:9])[CH:11]=3)[N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 661742-Amino-5-chloropyridineHCID 150783Isopropyl isocyanideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 74763778HCID 74763778, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloropyridin-2-amine (130 mg, 1.01 mmol), 3-chlorobenzaldehyde (171 mg, 1.21 mmol) and p-toluenesulfonic acid monohydrate (77 mg, 0.40 mmol) were combined in 2 mL of methanol to give a clear solution. To this solution was added 2-isocyanopropane (78 mg, 1.13 mmol) and the resulting clear solution was stirred at room temperature for 45 minutes. The mixture was filtered and the white solid was rinsed with methanol three times. The white solid was dried to afford [6-chloro-2-(3-chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-isopropyl-amine (48 mg, 15%). MS: 320.0 and 322.0 [M+H]+; 1H-NMR (DMSO-d6): δ 8.53 (s, 1H), 8.23 (s, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.32 (d, 1H), 7.20 (d, 1H), 4.92 (d, 1H), 3.20 (m, 1H), 1.04 (d, 6H).

Workup

  1. customto give a clear solution
  2. filtrationThe mixture was filtered
  3. washthe white solid was rinsed with methanol three times
  4. customThe white solid was dried

Sources & evidence

ORD record
ord-2289c93b6f6e4c50be120e5311913173
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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