Diisopropylethylamine → HCID 178473956, compound

HRID 858300Notes

Reaction equation

HRID 858300 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[CH2:6][C:5]1=[O:14])(=[O:3])[CH3:2].[CH3:15][N:16]1[C:20]2[CH:21]=[CH:22][C:23]([C:25](O)=[O:26])=[CH:24][C:19]=2[N:18]=[CH:17]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:6](=[C:25]([OH:26])[C:23]2[CH:22]=[CH:21][C:20]3[N:16]([CH3:15])[CH:17]=[N:18][C:19]=3[CH:24]=2)[C:5]1=[O:14])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 49130631-Methyl-1H-benzimidazole-5-carboxylic acidHCID 116441611-Acetyl-6-chloro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 178473956HCID 178473956, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.5 g of 1-acetyl-6-chloro-2-indolinone, 3.4 g of 1-methylbenzimidazole-5-carboxylic acid, 6.1 g of TBTU, 2.9 g of HOBT-hydrate and 8.7 ml ethyldiisopropylamine are stirred in 100 ml DMF for 15 hours at ambient temperature. The mixture is combined with water and extracted with ethyl acetate, while the crude product is partially precipitated. The residue obtained by distilling off the solvent is taken up in dichloromethane and a little methanol and extracted with water. The organic phase is evaporated down, the residue stirred successively with ethyl acetate and diethyl ether, suction filtered and dried.

Workup

  1. extractionextracted with ethyl acetate, while the crude product
  2. customis partially precipitated
  3. customThe residue obtained
  4. distillationby distilling off the solvent
  5. extractiona little methanol and extracted with water
  6. customThe organic phase is evaporated down
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-7edb584066814722a69e407c4a7261c6
Source dataset
uspto-grants-2006_12
Patent number
US07148249B2

Reaction notes

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