Chlorosuccinimide → HCID 86654727, compound

HRID 2092837Notes

Reaction equation

HRID 2092837 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([NH:26][C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)=[N:8][C:9]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][C:5]=2[CH2:4][NH:3]1.[Cl:34]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:34][C:10]1[C:5]2[CH2:4][NH:3][C:2](=[O:1])[C:6]=2[C:7]([NH:26][C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)=[N:8][C:9]=1[NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86654728HCID 86654728, compound

Product 1

HCID 86654727HCID 86654727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A vial was charged with tert-butyl (1S,2R)-2-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (63 mg, 0.140 mmol) and N-chlorosuccinimide (18.63 mg, 0.140 mmol) in DCM (1.4 mL) to give a yellow solution. The solution was stirred for 1 h at RT. The crude reaction mixture was diluted with DCM (20 mL) and washed with saturated aq NaHCO3 (2×10 mL) followed by water (10 mL) and brine (10 mL). The organic layers were combined, dried over sodium sulfate, and concentrated to a residue which was purified by flash column chromatography. The collected fractions were concentrated to a brown residue to give the title compound as a cream colored solid upon drying (38.1 mg, 56%). [M+H] calc'd for C25H32ClN5O3, 486. found, 486.

Workup

  1. customto give a yellow solution
  2. customThe crude reaction mixture
  3. washwashed with saturated aq NaHCO3 (2×10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a residue which
  6. customwas purified by flash column chromatography
  7. concentrationThe collected fractions were concentrated to a brown residue

Sources & evidence

ORD record
ord-20482e9dab624b308b5b8bac304870dd
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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