Sodium Hydroxide → HCID 18466636, compound

HRID 2229326Notes

Reaction equation

HRID 2229326 reaction equation
N[C:2]1[CH:3]=[C:4]([CH3:21])[C:5]2[NH:6][C:7](=[O:20])[C:8]3[CH:18]=[C:17]([Br:19])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.C1C=CN=CC=1.[FH:28].N([O-])=O.[Na+].[OH-].[Na+]>>[Br:19][C:17]1[CH:16]=[N:15][C:9]2[N:10]([CH2:13][CH3:14])[C:11]3[N:12]=[C:2]([F:28])[CH:3]=[C:4]([CH3:21])[C:5]=3[NH:6][C:7](=[O:20])[C:8]=2[CH:18]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 64774Pyridine, hydrofluoride (1:1)HCID 18466632HCID 18466632, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18466636HCID 18466636, compoundYield 84%

Conditions

Temperature
0 °C

Procedure

A plastic bottle was charged with 2-amino-8-bromo-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (5.10 g, 14.6 mmol). HF-pyridine (100 g) was added and the resulting suspension was cooled to 0° C. Sodium nitrite (1.12 g, 16.1 mmol) was added in several portions over 30 min to produce a purple solution. The mixture was then stirred for 16 h at room temperature. The reaction mixture was poured onto ice and 6 N NaOH. The beige suspension was extracted with EtOAc. The organic extracts were combined, dried over MgSO4, filtered and concentrated. The residue was triturated with Et2O/hexane to give the title compound (4.30 g, 84% yield).

Workup

  1. customto produce a purple solution
  2. extractionThe beige suspension was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with Et2O/hexane

Sources & evidence

ORD record
ord-25fae6f428f34cfb88fdb986353ca59b
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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