Diisopropylethylamine → HCID 66772830, compound

HRID 1645282Notes

Reaction equation

HRID 1645282 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[O:17][C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][C:19]=2[F:27])=[CH:15][CH:14]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:61][N:62]1[CH2:68][CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[O:17][C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([N:65]3[CH2:66][CH2:67][CH2:68][N:62]([CH3:61])[CH2:63][CH2:64]3)=[O:23])=[CH:20][C:19]=2[F:27])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66772741HCID 66772741, compound

Product 1

HCID 66772830HCID 66772830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoic acid (40 mg, 0.104 mmol) in DMF was added HBTU (60 mg, 0.157 mmol) and DIEA (55 μL, 0.313 mmol). The mixture was stirred at room temperature then was added 1-methylhomopiperazine (16 μL, 0.125 mmol) and allowed to stir at room temperature. The solid formed was isolated by filtration and purified by HPLC to yield 5-chloro-3-((5-(2-fluoro-4-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)methylene)indolin-2-one. LCMS (M+1=480).

Workup

  1. stirringto stir at room temperature
  2. customThe solid formed
  3. customwas isolated by filtration
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-4833769a6f64408d895e4132ac11a9be
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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