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

HRID 1947881Notes

Reaction equation

HRID 1947881 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>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:20]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[C:13]2[C:17]=1[C:16](=[O:18])[N:15]([CH3:19])[CH2:14]2)([CH3:4])([CH3:3])[CH3:2]

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-5c5535012d474db0b6272cf68b6880c5
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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