Dichloromethane → HCID 68614655, compound

HRID 1943244Notes

Reaction equation

HRID 1943244 reaction equation
[NH2:1][CH2:2][C@@H:3]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]1.[S:23]1[C:31]2[CH:30]=[C:29]([CH:32]=O)[N:28]=[CH:27][C:26]=2[O:25][CH2:24]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:56]>CO.CO.C(Cl)Cl>[ClH:56].[ClH:56].[S:23]1[C:31]2[CH:30]=[C:29]([CH2:32][NH:1][CH2:2][C@@H:3]3[CH2:7][CH2:6][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)[CH2:4]3)[N:28]=[CH:27][C:26]=2[O:25][CH2:24]1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 59254367[1,3]Oxathiolo[5,4-c]pyridine-6-carbaldehydeHCID 68596242HCID 68596242, compound

Product 1

HCID 68614655HCID 68614655, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a 10 mL round-bottomed flask were added (1R)-1-{[(3S)-3-(aminomethyl)-1-pyrrolidinyl]methyl}-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (60 mg, 0.200 mmol), [1,3]oxathiolo[5,4-c]pyridine-6-carbaldehyde (33.4 mg, 0.200 mmol) (for a synthesis see WO2004058144 Example 61), and sodium sulfate (250 mg, 1.760 mmol) in DCM (4 ml) and methanol (1.00 ml) to give an orange suspension. The reaction was stirred overnight under nitrogen. Sodium triacetoxyborohydride (85 mg, 0.400 mmol) was added and the reaction was stirred for 3 h. The reaction mixture was diluted with 10% MeOH/DCM (20 mL), filtered, adsorbed onto silica and then purified by silica chromatography eluting with 0-10% MeOH/DCM (1% NH4OH) to give the free base of the title compound as a yellow oil. LCMS/NMR consistent with the desired product.

Workup

  1. customto give an orange suspension
  2. stirringthe reaction was stirred for 3 h
  3. filtrationfiltered
  4. custompurified by silica chromatography
  5. washeluting with 0-10% MeOH/DCM (1% NH4OH)

Sources & evidence

ORD record
ord-8b5c958ffaab4c40ba6a240aaa0ae044
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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