Pyrrolidine → tert-butyl[2-methyl-3-oxo-7-(pyrrolidin-1-ylcarbonyl)-2,3-dihydro-1H-isoindol-4-yl]carbamate

HRID 511312Notes

Reaction equation

HRID 511312 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH3:19])[CH2:14][C:13]=2[C:12]([C:20]([OH:22])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[CH3:19][N:15]1[C:16](=[O:18])[C:17]2[C:13](=[C:12]([C:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:11]=[CH:10][C:9]=2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14]1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 672564057-[(Tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid2×

Product 1

HCID 86654017tert-butyl[2-methyl-3-oxo-7-(pyrrolidin-1-ylcarbonyl)-2,3-dihydro-1H-isoindol-4-yl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-[(Tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid (Compound 116C, 45 mg, 0.15 mmol), pyrrolidine (123 uL, 1.47 mmol), TBTU (236 mg, 0.734 mmol), DIPEA (128 uL, 0.734 mmol) and DMF (1 mL) were mixed and stirred at room temperature for 2 hours. The reaction mixture was diluted with EtOAc and washed with water (2×) and brine. The crude product was purified by column chromatography. MS (ES+): m/z 360.34 (100) [MH+]; HPLC: tR=1.20 min (UPLC, Analytical).

Workup

  1. washwashed with water (2×) and brine
  2. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e963b2373c564451beea8911cdf7a329
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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