Piperidine → HCID 86624702, compound

HRID 604917Notes

Reaction equation

HRID 604917 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]2[S:23][C:24]([CH:27]=O)=[CH:25][N:26]=2)[CH:12]=[CH:13][C:14]=1[N:15]1[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]1>>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]2[S:23][C:24]([CH2:27][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:25][N:26]=2)[CH:12]=[CH:13][C:14]=1[N:15]1[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 86624700HCID 86624700, compound

Product 1

HCID 86624702HCID 86624702, compound

Procedure

The title compound was prepared in analogy to example 57 from 16 mg (0.19 mmol) piperidine and 65 mg (0.21 mmol) 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-5-carbaldehyde. The reaction was not complete and the same amount of reagent was added like in example 57. The crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 36 mg (50%) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(5-piperidin-1-ylmethyl-thiazol-2-yl)-amine as a yellow oil. MS ISP (m/e): 384.3 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=7.64 (s, 1H), 7.25 (d, 1H), 7.18 (d, 1H), 7.08 (s, 1H), 6.96 (d, 1H), 6.87 (s, 1H), 3.85 (s, 3H), 3.59 (s, 2H), 2.42 (m, 4H), 2.30 (s, 3H), 1.59-1.54 (m, 4H), 1.45-1.43 (m, 2H).

Workup

  1. additionthe same amount of reagent was added like in example 57
  2. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 36 mg (50%) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(5-piperidin-1-ylmethyl-thiazol-2-yl)-amine as a yellow oil

Sources & evidence

ORD record
ord-ec614a63bef846dfb24791563908cb4e
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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