Dichloromethane → HCID 68600654, compound

HRID 1943230Notes

Reaction equation

HRID 1943230 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[CH:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.[F:23][C:24]1[C:32]2[N:31]=[C:30]([CH:33]=O)[NH:29][C:28]=2[CH:27]=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:62]>CO>[ClH:62].[ClH:62].[F:23][C:24]1[C:32]2[N:31]=[C:30]([CH2:33][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][C@H:9]4[N:19]5[C:20]6[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=6[CH:16]=[CH:17][C:18]5=[O:21])[CH2:10]4)[CH2:6][CH2:7]3)[NH:29][C:28]=2[CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 6

HCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218736341H-Benzimidazole-2-carboxaldehyde,4-fluoro-(9CI)HCID 58001796(1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

Product 1

HCID 68600654HCID 68600654, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 10 mL round-bottomed flask were added (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (for a preparation see Example 5A(j)) (80 mg, 0.238 mmol), 4-fluoro-1H-benzimidazole-2-carbaldehyde (for a synthesis see WO2003087098, Example 320) (42.9 mg, 0.261 mmol), and sodium bicarbonate (100 mg, 1.190 mmol) in DCM (4 ml) and methanol (1 ml) to give a brown suspension. Sodium sulfate (200 mg, 1.408 mmol) was added and the reaction was stirred at rt overnight. After 15 h sodium triacetoxyborohydride (101 mg, 0.475 mmol) was added and the reaction was stirred at 25° C. under nitrogen for 4 h. The reaction mixture was adsorbed onto silica and purified using 0-10% MeOH/DCM (1% NH4OH) to give the free base of the title compound. The LCMS and 1H NMR were consistent with the desired product.

Workup

  1. customto give a brown suspension
  2. stirringthe reaction was stirred at 25° C. under nitrogen for 4 h
  3. custompurified

Sources & evidence

ORD record
ord-3f64e322041941fdbe19406d555221a8
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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