L-Tartaric acid → HCID 11696864, compound

HRID 899345Notes

Reaction equation

HRID 899345 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:15][C@@H:14]3[C@@H:11]([CH2:12][NH:13]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8].[C:16]([OH:25])(=[O:24])[C@@H:17]([C@H:19]([C:21]([OH:23])=[O:22])[OH:20])[OH:18]>CO>[C:21]([C@@H:19]([C@H:17]([C:16]([OH:25])=[O:24])[OH:18])[OH:20])([OH:23])=[O:22].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:15][C@@H:14]3[C@@H:11]([CH2:12][NH:13]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 10131048Sofinicline

Product 1

HCID 11696864HCID 11696864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the product of Example 5J (442 mg) in 5 mL methanol was slowly added a solution of L-tartaric acid (272 mg) in methanol (2 mL). During the addition, solids started to crystallize. Upon completion of the addition, the slurry was stirred at room temperature for 10 minutes. The resulting mixture was then filtered and air-dried on the filter. 1H NMR (D2O, 400 MHZ) δ 3.04 (dd, J=10, 6 Hz, 1H), 3.21 (dd, J=13, 5 Hz, 1H), 3.50–3.56 (m, 2H), 3.73 (m, 1H) 3.83 (d, J=11 Hz, 1H), 4.07 (d, J=13 Hz, 1H) 4.29 (m, 1H), 4.48 (s, 2H), 5.11 (m, 1H), 7.49 (d, J=3 Hz, 1H), 7.85 (d, J=3 Hz, 1H).

Workup

  1. additionDuring the addition, solids
  2. customto crystallize
  3. additionUpon completion of the addition
  4. filtrationThe resulting mixture was then filtered
  5. customair-dried on the filter

Sources & evidence

ORD record
ord-e7515563512e422f8a06f35168e76752
Source dataset
uspto-grants-2008_04
Patent number
US07354937B2

Reaction notes

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