Diisopropylethylamine → HCID 66772399, compound

HRID 1645281Notes

Reaction equation

HRID 1645281 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:19]=[C:20]([CH:24]=[CH:25][C:26]=2[F:27])[C:21](O)=[O:22])=[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:19]=[C:20]([C:21]([N:65]3[CH2:66][CH2:67][CH2:68][N:62]([CH3:61])[CH2:63][CH2:64]3)=[O:22])[CH:24]=[CH:25][C:26]=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 66772234HCID 66772234, compound

Product 1

HCID 66772399HCID 66772399, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-4-fluorobenzoic acid (39 mg, 0.102 mmol) in DMF was added HBTU (58 mg, 0.153 mmol) and DIEA (53 μL, 0.306 mmol). The mixture was stirred at room temperature then was added 1-methylhomopiperazine (16 μL, 0.122 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-5-(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-d3d2fee6cbce4b5bb82eed4e6b9e65aa
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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