Diisopropylethylamine → HCID 86663257, compound

HRID 337137Notes

Reaction equation

HRID 337137 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:14][C:15]1[C:16](=[O:32])[N:17]([C:21]2[CH:22]=[C:23]([CH:27]=[C:28]([F:31])[C:29]=2[CH3:30])[C:24]([OH:26])=O)[CH:18]=[CH:19][N:20]=1)([CH3:13])[CH3:12].F[B-](F)(F)F.[N:38]1([O:47][C:48](N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CON>CN(C=O)C.O>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:14][C:15]1[C:16](=[O:32])[N:17]([C:21]2[CH:22]=[C:23]([CH:27]=[C:28]([F:31])[C:29]=2[CH3:30])[C:24]([NH:38][O:47][CH3:48])=[O:26])[CH:18]=[CH:19][N:20]=1)([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66689941HCID 66689941, compound

Product 1

HCID 86663257HCID 86663257, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 3-[3-({1-[2-(2-chloroethoxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-5-fluoro-4-methylbenzoic acid (Example 316c, 0.13 g) in DMF (3 mL) was added O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (0.182 g) and N,N-diisopropylethylamine (0.148 mL). The reaction was stirred for 15 min, then O-methylhydroxylamine hydrochloride (0.047 g) was added. The reaction mixture was stirred at room temperature overnight, then diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated to afford the subtitle compound (0.13 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-74ce32253bd34f4a956fc61cce77192c
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

Loading…