Sodium triacetoxyborohydride → HCID 178452762, compound

HRID 81094Notes

Reaction equation

HRID 81094 reaction equation
[NH2:1][C:2]1[C:3]([Cl:17])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH:25]=O)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:17][C:3]1[C:2]([NH:1][CH2:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]2)=[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:6]=[C:5]([Cl:16])[N:4]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86724467Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamateHCID 178461263HCID 178461263, compound

Product 1

HCID 178452762HCID 178452762, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate (353 g, 1.27 mol) and trans-4-methylcyclohexanecarbaldehyde (160 g, 1.27 mol) in DCM (8.0 L) and acetic acid (2 ml) was added sodium triacetoxyborohydride (807.7 g, 3.81 mol) at 0° C. The mixture was stirred for 15 min, and then warmed to room temperature. The mixture was stirred for 15 h at room temperature and then quenched with water (10 L). The mixture was filtered, the filtrate was separated, and the organic layer was concentrated under reduced pressure to give crude product. The crude product was purified over a silica gel column, eluting with EtOAc: petroleum ether (0-1:10), to give tert-butyl (2,6-dichloro-3-(((trans-4-methylcyclohexyl)methyl)amino)pyridin-4-yl)carbamate.

Workup

  1. stirringThe mixture was stirred for 15 h at room temperature
  2. customquenched with water (10 L)
  3. filtrationThe mixture was filtered
  4. customthe filtrate was separated
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customto give crude product
  7. customThe crude product was purified over a silica gel column
  8. washeluting with EtOAc: petroleum ether (0-1:10)

Sources & evidence

ORD record
ord-2e2147643ee740edbd6d3d744142f8be
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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