Pyridine → HCID 57586409, compound

HRID 2190348Notes

Reaction equation

HRID 2190348 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([NH:13][C:14](=[O:39])[N:15]([CH2:24][CH2:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:27]1([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:25][CH2:24][N:15]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:14]([NH:13][C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:46](=[O:48])[CH3:47])=[CH:7][CH:6]=3)[S:12][N:11]=2)=[O:39])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic Anhydride2×HCID 57586382HCID 57586382, compound

Product 1

HCID 57586409HCID 57586409, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-aminophenyl)-1,2,4-thiadiazol-3-yl)-1-(3,3-diphenylpropyl)-1-(2-(pyridin-2-yl)ethyl)urea (0.042 g, 0.079 mmol), prepared in the previous step, in DCM (1.5 mL) at 0° C. was added pyridine (50 μL, 49 mg, 0.62 mmol) and acetic anhydride (9.0 μL, 9.0 mg, 0.088 mmol). The reaction mixture was warmed to room temperature. After 1 h, additional acetic anhydride (10 μL) and a small amount of DMAP were added. Stirring was continued at room temperature. After 3 h, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. The crude reaction mixture was dissolved in DCM (˜2 mL) and diluted with ˜5 mL of hexanes. The precipitate was collected by filtration and dried under high vacuum to give N-(4-(3-(((3,3-diphenylpropyl)(2-(2-pyridinyl)ethyl)carbamoyl)amino)-1,2,4-thiadiazol-5-yl)phenyl)acetamide 158. Mass spectrum, calculated for C33H32N6O2S 576.2; found 577.2 (M++1).

Workup

  1. customwas continued at room temperature
  2. waitAfter 3 h
  3. washwashed with saturated NaHCO3 (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude reaction mixture
  8. filtrationThe precipitate was collected by filtration
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-199d8bf29e394209a2db7678dde90cc3
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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