Dichloromethane → HCID 59362713, compound

HRID 1625461Notes

Reaction equation

HRID 1625461 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]([CH2:23][CH2:24][CH2:25][CH: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]([CH2:23][CH2:24][CH2:25][CH: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 2

HCID 6344DichloromethaneHCID 86642418HCID 86642418, compound

Product 1

HCID 59362713HCID 59362713, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

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)-1,2,3,4-tetrahydro-naphthalen-1-yl]-amide (0.063 g, 0.000097 mol;) was dissolved in 0.5 M of Sodium methoxide in methanol (3 mL) and Methylene chloride (3 g, 0.04 mol;) and heated at 75 C for 1 hour. LC-MS showed the disappearance of starting material and the appearance of product. The reaction was concentrated and dissolved in DMSO and methanol 1:1 for purification by Gilson Preparative HPLC. Pure fractions were combined and concentrated to give the pure product. ES (+) MS m/e=511.37; (400 MHz, DMSO-d6) δ ppm 1.84 (m, 3H), 2.07 (m, 1H), 2.80 (m, 2H), 5.22 (d, 2H, 5 Hz), 5.25 (m, 1H), 6.62 (t, 1H, J=8 Hz), 6.99 (m, 1H), 7.12 (m, 1H), 7.20 (d, 1H, J=8 Hz), 7.30-7.45 (m, 2H), 7.52 (m, ′H), 7.60 (s, 1H), 7.78 (s, 1H), 8.16 (d, 1H, J=8 Hz), 8.22 (m, 2H), 8.46 (m, 1H), 10.10 (d. 1H, J=8 Hz), 12.55 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in DMSO
  3. custommethanol 1:1 for purification by Gilson Preparative HPLC
  4. concentrationconcentrated
  5. customto give the pure product

Sources & evidence

ORD record
ord-c9c6618bc0a94163b00a9115b71137bc
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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