Diisopropylethylamine → (5-(3-(3-tert-butyl-1,2,4-thiadiazol-5-ylamino)pyridin-2-yloxy)-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone

HRID 2390516Notes

Reaction equation

HRID 2390516 reaction equation
[NH2:1][C:2]1[C:3]([O:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][CH2:13][N:14]3[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:27](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:28].[C:43]([NH2:49])(=[NH:48])[C:44]([CH3:47])([CH3:46])[CH3:45].CCN(C(C)C)C(C)C.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[C:44]([C:43]1[N:49]=[C:27]([NH:1][C:2]2[C:3]([O:8][C:9]3[CH:18]=[CH:17][CH:16]=[C:15]4[C:10]=3[CH2:11][CH2:12][CH2:13][N:14]4[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:20])=[N:4][CH:5]=[CH:6][CH:7]=2)[S:28][N:48]=1)([CH3:47])([CH3:46])[CH3:45]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 431752Pivalamidine hydrochlorideHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 5462977Diethyl azodicarboxylateHCID 59128866(5-(3-aminopyridin-2-yloxy)-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone

Product 1

HCID 59128976(5-(3-(3-tert-butyl-1,2,4-thiadiazol-5-ylamino)pyridin-2-yloxy)-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanoneYield 14.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-(3-aminopyridin-2-yloxy)-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone (Example A171d) (224 mg, 0.58 mmol), 1,1′-thiocarbonyldi-2(1H)-pyridone (269 mg, 1.16 mmol) in DCM (10 mL) was agitated at rt for 4 h. The mixture was evaporated and diluted in THF (5 mL), pivalamidine (79 mg, 0.58 mmol) and DIPEA (205 μL, 1.16 mmol) were added and mixture was heated at 80° C. in a sealed tube for 24 h. The solution was cooled down and DEAD (183 μL, 1.16 mmol) was added, mixture was stirred for 2 h. The reaction mixture was evaporated in vacuo and purified using preparative HPLC to afford the final product (40 mg). (M+H)+=486.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted in THF (5 mL)
  3. temperaturemixture was heated at 80° C. in a sealed tube for 24 h
  4. temperatureThe solution was cooled down
  5. stirringmixture was stirred for 2 h
  6. customThe reaction mixture was evaporated in vacuo
  7. custompurified

Sources & evidence

ORD record
ord-a73b9dfcd1a2460186c5b607dbe503e7
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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