Diisopropylethylamine → HCID 59355020, compound

HRID 2196403Notes

Reaction equation

HRID 2196403 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:44][C@@H:45]([CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=1[C:65]([F:68])([F:67])[F:66])[CH2:46][N:47]1[C:55](=[O:56])[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]1=[O:57]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:44][C@@H:45]([CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]([F:68])([F:66])[F:67])[CH2:46][N:47]2[C:55](=[O:56])[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]2=[O:57])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 2733179PyBroPHCID 578268082-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59355020HCID 59355020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-pyridinecarboxylic acid (97 mg, 2.6 mmol), PyBrOP (269 mg, 0.578 mmol) and diisopropylethyl amine (419 uL, 2.41 mmol) in DCM (5 mL) at 25° C. was added 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione (168 mg, 0.481 mmol)[prepared in preparation 3]. After 16 h, the solution was partitioned between H2O and washed with DCM. The combined organic fraction were dried (Na2SO4), concentrated and used directly without further purification: LC-MS (ES) m/z=435 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O
  2. washwashed with DCM
  3. dry with materialThe combined organic fraction were dried (Na2SO4)
  4. concentrationconcentrated
  5. customused directly without further purification

Sources & evidence

ORD record
ord-8bc051fa2b9648a39db7cb2ce47f6e5b
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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