Sodium Bicarbonate → HCID 131730676, compound

HRID 445239Notes

Reaction equation

HRID 445239 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:39]=[CH:38][C:18]([CH2:19][N:20]2[C@H:24]([C:25](O)=O)[CH2:23][C:22]3([CH2:32][CH2:31][N:30]([CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH2:29][CH2:28]3)[CH2:21]2)=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.O.N.C[NH3+].F[P-](F)(F)(F)(F)F.N1([O:60][C:61](N(C)C)=[N+:62](C)C)C2C=CC=NC=2N=N1.F[P-](F)(F)(F)(F)F.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C@H:24]([CH2:25][C:61]([NH2:62])=[O:60])[CH2:23][C:22]3([CH2:28][CH2:29][N:30]([CH:33]([CH2:34][CH3:35])[CH2:36][CH3:37])[CH2:31][CH2:32]3)[CH2:21]2)=[CH:38][CH:39]=1)[CH2:6][C:2]1[NH:3][CH:4]=[CH:5][N:1]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 12896473Azane;hydrateHCID 49854554HCID 49854554, compoundHCID 131730677HCID 131730677, compound

Product 1

HCID 131730676HCID 131730676, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, the compound (315 mg) obtained in Example 32(7) was dissolved in dimethylformamide (3 mL), and then 28% ammonia water (199 μL) and HATU (2-(1H-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methaneaminium) (337 mg) were added, followed by stirring at room temperature for 15 hours. After completion of the reaction, water (10 mL) and then an aqueous saturated sodium hydrogen carbonate were added, followed by extraction twice with dichloromethane (20 mL). The organic layers were combined, washed with saturated brine and then dried over anhydrous magnesium sulfate. After removing anhydrous magnesium sulfate by filtration, the filtrate was concentrated and the resultant residue was purified by silica gel column chromatography (CHROMATOREX NH (trade name), manufactured by Fuji Silysia Chemical Ltd.) (hexane:ethyl acetate=50:50→0:100→ethyl acetate:methanol=100:0→80:20) to obtain the title compound having the following physical properties (yield: 204 mg).

Workup

  1. extractionfollowed by extraction twice with dichloromethane (20 mL)
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customthe resultant residue was purified by silica gel column chromatography (CHROMATOREX NH (trade name), manufactured by Fuji Silysia Chemical Ltd.) (hexane:ethyl acetate=50:50→0:100→ethyl acetate:methanol=100:0→80:20)

Sources & evidence

ORD record
ord-7bfc5ba4b41f4f6ebe8bec6befe99584
Source dataset
uspto-grants-2013_07
Patent number
US08476290B2

Reaction notes

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