1,2-Dichloroethane → HCID 71768543, compound

HRID 1746907Notes

Reaction equation

HRID 1746907 reaction equation
[NH2:1][C:2](=[O:38])[CH:3]([OH:37])[CH:4]([NH:12][C:13](=[O:36])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH:35]=[C:23]2[CH2:24][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][CH2:27][C:22]2=[N:21]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(Cl)CCl.ClC(Cl)C(O)=O.C([O-])(O)=O.[Na+]>CS(C)=O.[Cl-].[Na+].O>[NH2:1][C:2](=[O:38])[C:3](=[O:37])[CH:4]([NH:12][C:13](=[O:36])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH:35]=[C:23]2[CH2:24][N:25]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:26][CH2:27][C:22]2=[N:21]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6597Dichloroacetic AcidHCID 516892Sodium BicarbonateHCID 89851562HCID 89851562, compound

Product 1

HCID 71768543HCID 71768543, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(5-benzyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)nicotinamide (45 mg, 0.088 mmol) in DMSO (1200 μL) at room temperature, EDC (160 mg, 0.835 mmol) was added, and after 5 min of stirring 2,2-dichloroacetic acid (40 μL, 0.487 mmol). The mixture was stirred for 45 min at room temperature, and then 10 mL of brine and 10 mL of saturated aqueous NaHCO3-solution were added, the precipitate formed filtered off and dried in vacuo. The yellow solid obtained was crystallized from 2-propanol, the resulting precipitate washed and treated with MTB and n-pentane to afford 27 mg of an off-white amorphous solid; ESI-MS [M+H]+: 509.2. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.86 (m, 1H), 8.47 (m, 1H), 8.07 (m, 1H), 7.98 (m, 1H), 7.76 (m, 1H), 7.65 (m, 1H), 7.35-7.18 (m, 11H), 5.33 (m, 1H), 4.05 (m, 1H), 3.68 (s, 2H), 3.45-3.16 (m, overlapping with water), 2.91 (dd, 1H), 2.72 (m, 4H).

Workup

  1. customthe precipitate formed
  2. filtrationfiltered off
  3. customdried in vacuo
  4. customThe yellow solid obtained
  5. customwas crystallized from 2-propanol
  6. washthe resulting precipitate washed
  7. additiontreated with MTB and n-pentane

Sources & evidence

ORD record
ord-b0dc48707c7a4db9b1d347a7cd1c44e6
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

Loading…