3-Pyridineacetic acid → HCID 44217479, compound

HRID 1931481Notes

Reaction equation

HRID 1931481 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[F:42][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[CH:48]([NH:52][C:53]1[CH:62]=[CH:61][C:60]3[C:55](=[CH:56][CH:57]=[C:58]([NH2:63])[CH:59]=3)[N:54]=1)[CH2:47][CH2:46]2>ClCCl.CN(C)C=O.O>[F:42][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[CH:48]([NH:52][C:53]1[CH:62]=[CH:61][C:60]3[C:55](=[CH:56][CH:57]=[C:58]([NH:63][C:8](=[O:10])[CH2:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:59]=3)[N:54]=1)[CH2:47][CH2:46]2

Participants

8

Reactant 4

HCID 1083-Pyridineacetic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68638772HCID 68638772, compound

Product 1

HCID 44217479HCID 44217479, compoundYield 51.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-Pyridyl-acetic acid (112 mg, 0.82 mmol), N,N-diisopropyl ethyl amine (308 mg, 2.4 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (350 mg, 1.1 mmol) were dissolved in dichloromethane (20 mL) and dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 30 minutes. rac-N2-(5-Fluoro-indan-1-yl)-quinoline-2,6-diamine (2000 mg, 0.68 mmol) was added and stirred was continued overnight. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined organic phases were dried over sodium sulfate and evaporated. The crude product was recrystallized with dichloromethane. The title compound (144 mg, 51%) was obtained as an off-white solid; MS: m/e=413.4 (M+H+).

Workup

  1. stirringstirred
  2. waitwas continued overnight
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated
  6. customThe crude product was recrystallized with dichloromethane

Sources & evidence

ORD record
ord-d481c69e0f4543fba4d7dc6927f703a5
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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