Sodium Bicarbonate → HCID 68598425, compound

HRID 1943172Notes

Reaction equation

HRID 1943172 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH: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.[O:23]=[C:24]1[NH:29][C:28]2[CH:30]=[C:31]([CH:34]=O)[CH:32]=[CH:33][C:27]=2[S:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)(O)[O-].[Na+].[Cl:55]CCl.CO>>[ClH:55].[O:23]=[C:24]1[NH:29][C:28]2[CH:30]=[C:31]([CH2:34][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH: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)[CH:32]=[CH:33][C:27]=2[S:26][CH2:25]1

Participants

6

Reactant 5

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 21226129Dichloromethane methanolHCID 580017221-[(4-Amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

Product 1

HCID 68598425HCID 68598425, compoundYield 39%

Procedure

1-[(4-Amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (2:1 mixture of R:S, for a preparation see Example 11(d)) (60 mg, 0.2 mmol) and 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehyde (for a synthesis see WO2002056882, Example 6(c) (38.6 mg, 0.2 mmol) were dissolved in dichloromethane/methanol (2/0.1 ml) at room temperature under argon and stirred at room temperature for 1 h. This was then treated with NaBH(OAc)3 (85 mg, 0.4 mmol) and left to stir for 1 hour. A saturated solution of sodium bicarbonate (20 ml) was then added and the aqueous was extracted with 20% methanol/dichloromethane (3×35 ml). The combined organic extracts were dried on magnesium sulphate, filtered and evaporated. The crude product was purified by silica chromatography using a 0-20% methanol/dichloromethane gradient to provide the free base of the title compound as a yellow solid (37 mg, 39%).

Workup

  1. waitleft
  2. stirringto stir for 1 hour
  3. extractionthe aqueous was extracted with 20% methanol/dichloromethane (3×35 ml)
  4. customThe combined organic extracts were dried on magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-2e684b2a471943f29c75e42fc520d7eb
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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