Sodium Bicarbonate → HCID 72777781, compound

HRID 1987337Notes

Reaction equation

HRID 1987337 reaction equation
[Na].[NH2:2][OH:3].O.CO[C:7](=[O:37])[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][OH:36])[CH:9]=1.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:27][C:26]1[C:21]([CH:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:28]3[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=3)[N:15]2[CH2:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:2][OH:3])=[O:37])=[CH:9][C:10]=2[CH2:35][OH:36])=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5360545Sodium2×HCID 22235265HCID 22235265, compound2×HCID 67422025HCID 67422025, compound

Product 1

HCID 72777781HCID 72777781, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6212ChloroformSolvent

Procedure

To a stirred solution of sodium (320 mg, 14 mmol) in anhydrous MeOH (15 mL) was added NH2OH.H2O (550 mg, 7.9 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-hydroxymethyl-benzoic acid methyl ester (700 mg, 1.6 mmol) in anhydrous MeOH (7 mL). The mixture was stirred for 2 h, at which time TLC indicated that the reaction had stalled. A solution of sodium (320 mg, 14 mmol) and NH2OH.H2O (550 mg, 7.9 mmol) in anhydrous MeOH (8 mL) was added to the reaction mixture and stirring was continued for 2 hours. The reaction mixture was diluted with CHCl3 (100 mL) and poured into a saturated NaHCO3 solution (100 mL). The aqueous layer was extracted with CHCl3 (5×100 mL). The combined organic portions were concentrated to 100 mL, washed once with saturated NaHCO3 solution (20 mL), dried over Na2SO4, concentrated, and dried under high vacuum to give COMPOUND 45 (647 mg, 92%) as an off-white solid. 1H NMR (DMSO-d6) δ 1.46 (d, 2H, J=12.0 Hz), 1.69-1.84 (m, 1H), 2.01-2.11 (m, 1H), 2.48 (s, 6H), 3.59 (s, 2H), 4.13 (d, 2H, J=3.8 Hz), 4.40 (d, 2H, J=10.8 Hz), 4.79-4.85 (m, 1H), 5.74 (s, 1H), 6.84-6.91 (m, 3H), 7.06 (d, 1H, J=7.5 Hz), 7.18-7.28 (m, 3H), 8.14 (d, 2H, J=3.3 Hz), 8.75 (s br, 1H), 10.82 (s br, 1H); 13C NMR (D2O) δ 18.38(2), 24.40, 25.32(2), 55.27, 60.85(2), 64.75, 122.31(2), 123.64, 124.88, 126.82, 132.62, 137.64(2), 138.08, 143.18, 145.86(2), 158.58, 164.49; ES-MS m/z 447 (M+H). Anal. Calcd. For C26H30N4O3.1.1H2O: C, 66.96; H, 6.96; N, 12.01. Found: C, 66.95; H, 6.71; N, 11.66.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. extractionThe aqueous layer was extracted with CHCl3 (5×100 mL)
  4. concentrationThe combined organic portions were concentrated to 100 mL
  5. washwashed once with saturated NaHCO3 solution (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-cbdf9bc36e504717b6e7465df3f74ee2
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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