Diisopropylethylamine → HCID 86663257, compound

HRID 1697395Notes

Reaction equation

HRID 1697395 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-24e40ac5bd2c43f88564d84618b75e71
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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