Dichloromethane → HCID 59362796, compound

HRID 1625462Notes

Reaction equation

HRID 1625462 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:19]3[CH:28]=[C:27]4[C:22]([CH:23]=[CH:24][CH:25]=[C:26]4[NH:29][C:30]([C:32]4[C:33](=[O:47])[N:34]([CH2:38][C:39]5[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=5)[CH:35]=[CH:36][CH:37]=4)=[O:31])=[CH:21][CH:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C(Cl)Cl.C[O-].[Na+]>CO>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[CH:24][CH:25]=[C:26]3[NH:29][C:30]([C:32]3[C:33](=[O:47])[N:34]([CH2:38][C:39]4[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=4)[CH:35]=[CH:36][CH:37]=3)=[O:31])=[CH:21][CH:20]=2)=[CH:11]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 86642419HCID 86642419, compound

Product 1

HCID 59362796HCID 59362796, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid [7-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-naphthalen-1-yl]-amide (0.035 g, 0.000054 mol;) was dissolved in Methylene chloride (2 g, 0.02 mol;) and 0.5 M of Sodium methoxide in methanol (2 mL) then heated at 80 degrees for 1 hour. LC-MS showed the appearance of product at 1.64 506.91. The crude was concentrated and dissolved in a mixture of methanol and DMSO then directly injected onto the gilson for purification. The pure fractions were combined and concentrated to give the product. ES (+) MS m/e=506.91; (400 MHz, DMSO-d6) δ ppm 5.43 (s, 2H), 6.76 (t, 1H, J=8 Hz), 6.98 (d, 1H, J=8 Hz), 7.08 (m, 1H), 7.25 (m, 1H), 7.36-7.6 (m, 3H), 8.01 (d, 1H, J=8 Hz), 8.14 (s, 1H), 8.27 (m, 2H), 8.35 (m, 2H), 8.49 (s, 1H), 8.60 (m, 1H), 8.80 (d, 1H, J=8 Hz), 12.10 (s. 1H), 12.63 (s, 1H).

Workup

  1. concentrationThe crude was concentrated
  2. dissolutiondissolved in a mixture of methanol and DMSO
  3. customthen directly injected onto the gilson for purification
  4. concentrationconcentrated
  5. customto give the product

Sources & evidence

ORD record
ord-7627a40bbd1f4a81828d0696f1dbdf35
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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