Sodium Bicarbonate → HCID 72768218, compound

HRID 1987338Notes

Reaction equation

HRID 1987338 reaction equation
[Na].[NH2:2][OH:3].O.C[O:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH:20]([C:21]3[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:19][CH2:18][CH2:17][CH:16]2[C:28]2[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=2)=[C:10]([CH2:35][O:36][CH3:37])[CH:9]=1.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:34][C:33]1[C:28]([CH:16]2[CH2:17][CH2:18][CH2:19][CH:20]([C:21]3[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[N:15]2[CH2:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:2][OH:3])=[O:6])=[CH:9][C:10]=2[CH2:35][O:36][CH3:37])=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 22235265HCID 22235265, compoundHCID 67421978HCID 67421978, compound

Product 1

HCID 72768218HCID 72768218, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a stirred solution of sodium (100 mg, 4.2 mmol) in anhydrous MeOH (4 mL) was added NH2OH.H2O (260 mg, 3.7 mmol) followed by a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-3-methoxymethyl-benzoic acid methyl ester (170 mg, 0.37 mmol) in anhydrous MeOH (4 mL). The mixture was stirred for 16 hours, diluted with CHCl3 (50 mL) and poured into a saturated NaHCO3 solution (50 mL). The aqueous layer was extracted with CHCl3 (5×25 mL). The combined organic portions were dried over Na2SO4 and concentrated. The resultant crude material was purified on a silica gel column (10 g, eluted with 5% NH4OH/10% MeOH/CH2Cl2) and dried under high vacuum to give COMPOUND 46 (60 mg, 35%) as a white solid. 1H NMR (CDCl3) δ 1.57-1.71 (m, 2H), 1.80-2.14 (m, 2H), 2.31-2.40 (m, 2H), 2.44 (s, 6H), 3.25 (s, 3H), 3.61 (s, 2H), 4.12 (s, 4H), 6.61-6.71 (m, 1H), 6.74-6.84 (m, 2H), 6.88-6.97 (m, 1H), 7.20 (s, 3H), 8.22 (s, 2H), 9.85 (s br, 1H); ES-MS m/z 461 (M+H).

Workup

  1. extractionThe aqueous layer was extracted with CHCl3 (5×25 mL)
  2. dry with materialThe combined organic portions were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resultant crude material was purified on a silica gel column (10 g, eluted with 5% NH4OH/10% MeOH/CH2Cl2)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-6f2c107af48942839b4ebf11b5c5eb11
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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