2-Aminopyridine → HCID 22876181, compound

HRID 1376399Notes

Reaction equation

HRID 1376399 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:14](=[O:16])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

3

Reactant 2

HCID 104392-AminopyridineHCID 89857Boc-L-methionine

Product 1

HCID 22876181HCID 22876181, compound

Procedure

Condensation of N-tert-butoxycarbonyl-L-inethionine (1a) with 2-aminopyridine (2j) according to General Procedure A, resulted, after purification on a SILICA GEL column (hexane-acetone 3:1), in (3o) (C15H23N3O3S1, 62%), Rf=0.33 (hexane-acetone 3:1), m.p. 135°-137° C., [α]D23 =-28.2° (c 0.11, CHCl3), IR (KBr) ν: 432, 459, 471, 496, 527, 623, 681, 737, 775, 829, 847, 864, 924, 964, 999, 1028, 1053, 1099, 1165, 1252, 1283, 1304, 1366, 1389, 1435, 1462, 1532, 1580, 1603, 1674, 1711, 2363, 2832, 2915, 2953, 2974, 2999, 3046, 3127, 3262 cm-1, 1H NMR (CDCl3) δ: 8.647-8.655 (br s, 1H, Ar--NH), 8.264-8.290 (m, 1H, ArH), 8.1705 (d, 1H, J 8.1 Hz, ArH), 7.659-7.718 (m, 1H, ArH), 7.016-7.055 (m, 1H, ArH), 5.210-5.227 (m, 1H, NH), 4.440 (m, 1H, Hα), 2.540-2.638 (m, 2H, CH2γ), 2.138-2.253 (m, 1H, Hβ), 2.099 (s, 3H, CH3ε), 1.968-2.040 (m, 1H, Hβ), 1.436 (s, 9H, t-Bu); EIMS (70 eV) m/z (%): 325 (M+, 5).

Workup

  1. customresulted
  2. customafter purification on a SILICA GEL column (hexane-acetone 3:1)
  3. customin (3o) (C15H23N3O3S1, 62%), Rf=0.33 (hexane-acetone 3:1), m.p. 135°-137° C., [α]D23 =-28.2° (c 0.11, CHCl3), IR (KBr) ν

Sources & evidence

ORD record
ord-75a849d9d0c0453fb924f897ff4b6505
Source dataset
uspto-grants-1997_09
Patent number
US05663149

Reaction notes

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