Hydrochloric Acid → HCID 71262245, compound

HRID 540236Notes

Reaction equation

HRID 540236 reaction equation
[O:1]=[S:2]1(=[O:33])C2C=CC=CC=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C:24]([CH:26]3CC(=O)[NH:28][CH2:27]3)=[O:25])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:32])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.C(OI([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)OC(=O)C)(=O)C.Cl.[C:50](#N)C>O>[NH2:28][CH:27]1[CH2:50][N:23]([C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:32])[CH:19]=3)[N:14]=[C:13]([N:5]3[CH2:6][C:48]4[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=4[S:2](=[O:33])(=[O:1])[CH2:3][CH2:4]3)[CH:22]=2)[C:24](=[O:25])[CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 76724Iodobenzene diacetateHCID 71255614HCID 71255614, compound2×

Product 1

HCID 71262245HCID 71262245, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-5-oxopyrrolidine-3-carboxamide (100 mg, 0.22 mmol, byproduct of Example 47-2) in acetonitrile (2 mL) and water (2 mL) was added (diacetoxyiodo)benzene (91 mg, 0.28 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water, acidified with concentrated hydrochloride acid (12 N), and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1-10% methanol in dichloromethane) to give 10 mg of the product as a white solid. MS obsd. (ESI+) [(M+H)+] 437, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.94-7.87 (m, 2 H), 7.60 (td, J=1.2, 7.2 Hz, 1 H), 7.55 (d, J=8.8 Hz, 1 H), 7.47-7.43 (m, 2 H), 7.37 (dd, J=2.0, 8.8 Hz, 1 H), 7.22 (s, 1 H), 5.13 (s, 2 H), 4.42 (brs, 2 H), 4.02 (dd, J=2.0, 9.6 Hz, 1 H), 3.87 (td, J=3.6, 6.8 Hz, 1 H), 3.62 (dd, J=4.8, 9.6 Hz, 2 H), 3.45 (dd, J=3.2, 9.6 Hz, 1 H), 3.14-3.13 (m, 1 H), 2.85 (dd, J=7.2, 16.8 Hz, 1 H), 2.36 (s, 3 H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 1-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c867b77ec0a242bda4f5b54b6aea7c07
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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