4-(5-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-tert-butylindolin-1-yl)butanoic acid → 4-(5-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-tert-butyl-1H-indol-1-yl)butanoic acid

HRID 2038090Notes

Reaction equation

HRID 2038090 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:20]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1>C(#N)C.O.FC(C(O)=O)(F)F>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:20]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 591294814-(5-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-tert-butylindolin-1-yl)butanoic acid

Product 1

HCID 247634714-(5-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-tert-butyl-1H-indol-1-yl)butanoic acid

Reagents, catalysts & solvents 1

HCID 22145617Water TFA acetonitrileSolvent

Procedure

4-(5-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-tert-butyl indolin-1-yl)butanoic acid (130 mg, 0.28 mmol) was taken up in a mixture of acetonitrile-H2O-TFA. The solvent was removed under reduced pressure and the residue obtained was dissolved in CDCl3. After a brief exposition to daylight (5-10 min), the solution turned purple. The mixture was stirred open to the atmosphere at room temperature until complete disappearance of the starting material (8 h). Solvent was removed under reduced pressure and the residue was purified by reverse phase HPLC to give 4-(5-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-tert-butyl-1H-indol-1-yl)butanoic acid. 1 H NMR (400 MHz, CDCl3) δ 7.52(d, J=1.9 Hz, 1H), 7.18(d, J=2.1 Hz, 1H), 7.16(s, 1H), 7.03(dd, J=9.4, 1.9 Hz, 1H), 7.00-6.98(m, 2H), 6.85(d, J=7.9 Hz, 1H), 6.16(s, 1H), 6.02(s, 2H), 4.29-4.24(m, 2H), 2.48(dd, J=6.9, 6.9 Hz, 2H), 2.12-2.04(m, 2H), 1.69(dd, J=6.8, 3.7 Hz, 2H), 1.43(s, 9H), 1.09(dd, J=6.8, 3.7 Hz, 2H). MS (ESI) m/e (M+H+) 463.0.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue obtained
  3. dissolutionwas dissolved in CDCl3
  4. customto daylight (5-10 min)
  5. customSolvent was removed under reduced pressure
  6. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-7defbceb06bc44378668634be78ea384
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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