Diisopropylethylamine → HCID 70856330, compound

HRID 1850781Notes

Reaction equation

HRID 1850781 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[O:24][N:23]=[C:22]([CH:25]([CH3:27])[CH3:26])[N:21]=3)[CH2:16][CH2:15]2)[CH:5]=[C:4]([F:28])[C:3]=1[CH2:29][C:30]([OH:32])=O.Cl.[NH:34]1[CH2:37][CH:36]([OH:38])[CH2:35]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:28][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[O:24][N:23]=[C:22]([CH:25]([CH3:26])[CH3:27])[N:21]=3)[CH2:16][CH2:15]2)[CH:7]=[C:2]([F:1])[C:3]=1[CH2:29][C:30]([N:34]1[CH2:37][CH:36]([OH:38])[CH2:35]1)=[O:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70856332HCID 70856332, compound

Product 1

HCID 70856330HCID 70856330, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [(2,6-difluoro-4-{2-[(1S,2R)-2-{1-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}cyclopropyl]ethoxy}phenyl)acetic acid (35.0 mg, 0.078 mmol) (from example 2, step B) in 1 ml anhydrous DMF at RT was added azetidin-3-ol hydrochloride salt (8.53 mg, 0.078 mmol) and N,N-diisopropylethylamine (0.041 ml, 0.234 mmol). o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (59.2 mg, 0.156 mmol) was added into the solution and stirred at RT for 4 hrs. The reaction mixture was filtered and purified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 35-95% acetonitrile in 0.1% formic acid in water gradient) to give the title compound. LC/MS (m/z): 505.4 (M+H)+. GPR119 Human EC50: 0.96 nM

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 35-95% acetonitrile in 0.1% formic acid in water gradient)

Sources & evidence

ORD record
ord-37c4b18ae4c54a2790b7b6d17a981581
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

Loading…