1-Acetylpiperazine → tert-Butyl 4-[(4-acetylpiperazin-1-yl)methyl]-6-methoxypyridin-2-ylcarbamate

HRID 1355536Notes

Reaction equation

HRID 1355536 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1)=O.[C:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)(=[O:21])[CH3:20].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl>[C:19]([N:22]1[CH2:27][CH2:26][N:25]([CH2:1][C:3]2[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=2)[CH2:24][CH2:23]1)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 837951-AcetylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 18506791tert-Butyl 4-formyl-6-methoxypyridin-2-ylcarbamate

Product 1

HCID 18506936tert-Butyl 4-[(4-acetylpiperazin-1-yl)methyl]-6-methoxypyridin-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-formyl-6-methoxypyridin-2-ylcarbamate (15-3, 292 mg, 1.16 mmole) and 1-acetylpiperazine (178 mg, 1.39 mmole) in 2% glacial HOAc in CH2Cl2 (5 mL) was added NaBH(OAc)3 (270 mg, 1.27 mmole) at RT. After 1.5 hr the mixture was quenched with saturated NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 0-5% EtOH/EtOAc) gave the titled compound as a white foam. 1H-NMR (500 MHz, CDCl3) δ 7.41 (s, 1 H), 7.00 (bs, 1 H), 6.43 (s, 1 H), 3.83 (s, 3 H), 3.63 (bs, 2 H), 3.46 (bs, 4 H), 2.41 (m, 4 H), 2.08 (s, 3 H), 1.52 (s, 9 H); MS (ES) (M+H)+ 365.

Workup

  1. customAfter 1.5 hr the mixture was quenched with saturated NaHCO3
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9968338e75fd438b85285a6df5324eba
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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