Aniline → HCID 59378050, compound

HRID 1639571Notes

Reaction equation

HRID 1639571 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.NC1C=CC=CC=1.[CH2:32]([O:34][C:35](=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]([C:45]1[S:49][N:48]=[C:47]([CH3:50])[N:46]=1)[C:42](O)=[O:43])[CH3:33].C(N(CC)CC)C>ClCCl>[CH2:32]([O:34][C:35](=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]([C:45]1[S:49][N:48]=[C:47]([CH3:50])[N:46]=1)[C:42](=[O:43])[NH:8][C:12]1[CH:11]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:33]

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59378085HCID 59378085, compound

Product 1

HCID 59378050HCID 59378050, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.56 g, 1.48 mmol) and aniline (0.13 g, 1.35 mmol) in dichloromethane (10 mL) was added over 5 min the solution of crude 2-(3-methyl[1,2,4]thiadiazol-5-yl)octanedioic acid 8-ethyl ester (2021039) and triethylamine in dichloromethane. The resultant reaction mixture was then stirred at room temperature overnight before being quenched with citric acid (5 g) in water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic fractions were dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (3:1 hexane/ethyl acetate followed by 1:1 hexane/ethyl acetate) to afford 7-(3-methyl[1,2,4]thiadiazol-5-yl)-7-phenylcarbamoyl heptanoic acid ethyl ester (2021040) (310 mg, 52% over two steps) as a yellow oil.

Workup

  1. customThe resultant reaction mixture
  2. custombefore being quenched with citric acid (5 g) in water (50 mL)
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by flash chromatography (3:1 hexane/ethyl acetate followed by 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-99dbfdc429e7404891ced2d5eae0ab18
Source dataset
uspto-grants-2012_02
Patent number
US08110577B2

Reaction notes

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