Diisopropylethylamine → HCID 86660419, compound

HRID 1186173Notes

Reaction equation

HRID 1186173 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:44][C:45]1[CH:46]=[CH:47][C:48]([F:60])=[C:49]([C:51]23[CH2:58][CH:57]2[CH2:56][O:55][CH2:54][C:53](=[S:59])[NH:52]3)[CH:50]=1>ClCCl>[F:60][C:48]1[CH:47]=[CH:46][C:45]([NH:44][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:10])=[CH:50][C:49]=1[C:51]12[CH2:58][CH:57]1[CH2:56][O:55][CH2:54][C:53](=[S:59])[NH:52]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27628725-Chloro-2-picolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 76831217HCID 76831217, compound

Product 1

HCID 86660419HCID 86660419, compoundYield 198.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2-pyridinecarboxylic acid (60 mg, 0.38 mmol) and diisopropylethylamine (0.17 ml, 0.99 mmol) in dichloromethane (20 ml) at 23° C. was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (174 mg, 0.46 mmol), the mixture was stirred for 15 min, then (1SR,7RS)-1-(5-amino-2-fluoro-phenyl)-5-oxa-2-aza-bicyclo[5.1.0]octane-3-thione (intermediate B13A) (91 mg, 0.36 mmol) was added and the resulting light yellow solution was stirred for 1 h at 23° C. The reaction mixture was poured on ice cold sat. NaHCO3-solution and extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give a brown solid (280 mg, 168%), which was purified by silica gel column chromatography with dichloromethane/ethyl acetate to give the title compound as a light yellow solid (147 mg, 88%). MS (ISP): m/z=392.1 [(M+H)+] and 394 [(M+2+H)+].

Workup

  1. stirringthe resulting light yellow solution was stirred for 1 h at 23° C
  2. additionThe reaction mixture was poured on ice cold sat. NaHCO3-solution
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cfe6ad63a07f4dae997b4b3d05b95ebc
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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