2-Amino-4-methylpyridine → HCID 4645825, compound

HRID 541022Notes

Reaction equation

HRID 541022 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[OH:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2>CC#N.O>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH:15]([C:14]2[CH:17]=[CH:18][C:11]([C:10]([F:20])([F:19])[F:9])=[CH:12][CH:13]=2)[C:23]2[C:22]([OH:21])=[C:31]3[C:26]([CH:27]=[CH:28][CH:29]=[N:30]3)=[CH:25][CH:24]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 15332-Amino-4-methylpyridineHCID 19238-HydroxyquinolineHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 4645825HCID 4645825, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared by method B presented for the compound of Example 1 with the change that 2-amino-4-methyl-pyridine (Molar), 4-trifluoromethyl-benzaldehyde (Sigma) and 8-hydroxy-quinoline (Sigma) were used as starting materials. Product obtained: C23H18F3N3O; (MW; 409.1): yield 230 mg, (29.6%) m.p.: 104-107° C.; HPLC (CH3CN/H2O 70:30 Phenomenex C18 282 nm): Tr=7.61 min. 1H NMR 8 (DMSO) δ 2.18 (3H, s, CH3), 6.41(1H, d, J=5.1 Hz), 6.44 (1H, s, NH), 6.49 (1H, d, J=4.9 Hz), 7.07 (1H, d, J=9.2 Hz), 7.39 (1H, d, J=8.9 Hz), 7.49-7.54 (1H, m), 7.58 (2H, d, J=7.9 Hz), 7.63 (2H, d, J=8.3 Hz), 7.73 (1H, d, J=7.9 Hz), 7.85 (2H, d, J=7.9 Hz), 8.03-8.08 (1H, m), 8.12 (2H, d, J=8.5 Hz), 8.27 (1H, d, J=8.2 Hz). 8.81-8.86 (1H, m); 13C-NMR 8 (DMSO) δ 23.5 (CH3), 51.8 (NHCH), 109.5 (CH), 117.6 (CH), 121.8 (CH), 124.5 (Cq), 125.1 (CH), 125.6 2×CH), 126.8 (CH), 127.7 (2×CH), 127.8 (Cq), 130.1 (CH), 134.7 (Cq), 136.1 (CH), 138.1 (Cq), 148.2 (Cq), 148.5 (CH), 149.6 (Cq), 157.7 (CH), 161.6 (Cq), 166.3 (Cq).

Workup

  1. customProduct obtained
  2. customTr=7.61 min

Sources & evidence

ORD record
ord-7752c40bdb4c4c3cb62eb1c72767857e
Source dataset
uspto-grants-2014_10
Patent number
US08871937B2

Reaction notes

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