Diisopropylethylamine → HCID 68753682, compound

HRID 624139Notes

Reaction equation

HRID 624139 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17]2.C(N(C(C)C)CC)(C)C.[CH2:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][NH:40]1>ClCCl>[CH2:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][N:40]1[C:5]([NH:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17]2)=[O:11]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 422478IsoindolineHCID 22591361tert-butyl 5-amino-2,3-dihydro-1H-isoindole-2-carboxylate

Product 1

HCID 68753682HCID 68753682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a 250 mL round bottom flask was mixed at room temperature triphosgene (234 mg, 0.790 mmol) in anhydrous dichloromethane (25 mL). To this solution was added dropwise over 15 minutes, a slurry of tert-butyl 5-aminoisoindoline-2-carboxylate (500 mg, 2.134 mmol) and diisopropylethylamine (0.410 ml, 2.347 mmol) in anhydrous dichloromethane (20 mL). The mixture was stirred overnight at room temperature. A solution of isoindoline (0.242 ml, 2.134 mmol) and diisopropylethylamine (0.410 ml, 2.347 mmol) in anhydrous dichloromethane (20 mL) was added in one portion. The reaction stirred overnight at room temperature. The solvent was removed and the residue was purified by normal phase flash chromatography to provide the title compound.

Workup

  1. additionTo this solution was added dropwise over 15 minutes
  2. stirringThe reaction stirred overnight at room temperature
  3. customThe solvent was removed
  4. customthe residue was purified by normal phase flash chromatography

Sources & evidence

ORD record
ord-731444c619934fe19b46e31c3adffc1a
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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