Tetrahydrofuran → HCID 66699704, compound

HRID 388123Notes

Reaction equation

HRID 388123 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1.Cl[C:21]1[C:26]([N+]([O-])=O)=[CH:25][CH:24]=[C:23](Cl)[N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1([C@H](N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>>[C:11]1([C@H:9]([N:8]2[C:6]3=[N:7][C:2]([C:43]4[CH:42]=[CH:41][CH:40]=[C:21]5[C:26]=4[CH:25]=[CH:24][CH:23]=[N:22]5)=[CH:3][CH:4]=[C:5]3[NH:17][C:50]2=[O:49])[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 6431891-Phenethylamine, (+)-HCID 86626406HCID 86626406, compound

Product 1

HCID 66699704HCID 66699704, compoundYield 78%

Procedure

(R)-6-Chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine. To a solution of 2,6-dichloro-3-nitropyridine (1.0 g, 5.18 mmol) in tetrahydrofuran (8 mL) at −78° C. was added diisopropylethylamine (1.08 mL, 6.22 mmol) followed by (R)-1-phenylethanamine (0.75 g, 6.22 mmol) in tetrahydrofuran (2 mL). The reaction was kept at −78° C. for 2 h and then allowed to slowly warm to room temperature overnight. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to afford the title compound (1.12 g, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.67 (d, J=7.5, 1H), 8.43 (d, J=8.5, 1H), 7.46 (d, J=7.5, 2H), 7.35 (t, J=7.5, 2H), 7.25 (t, J=7.5, 1H), 6.80 (d, J=8.5, 1H), 5.38 (app quint, J=7, 1H), 1.59 (d, J=7, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e3e2db0b9eba4b4b8f9f65438f2a1e39
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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