HCID 131730324, compound → HCID 131730323, compound

HRID 1948317Notes

Reaction equation

HRID 1948317 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[C:20]([C:26]([N+:29]([O-])=O)=[CH:27][N:28]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:14][C@H:13]1[O:32][CH3:33])=[O:10]>Cl.C(O)(=O)C>[NH2:29][C:26]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][C:18]([N:15]2[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([C:3]3[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=3[Cl:1])=[O:10])[C@H:13]([O:32][CH3:33])[CH2:14]2)=[N:28][CH:27]=1

Participants

4

Reactant 1

HCID 131730324HCID 131730324, compound

Product 1

HCID 131730323HCID 131730323, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of SnCl2 dihydrate (870 mg, 3.8 mmol) in 5 ml concentrated HCl was added to a solution of 436 mg (0.87 mmol) of Cis(±)-ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-nitroisonicotinate (Example 308) in 30 ml acetic acid. The mixture was stirred at room temperature overnight. Solvent was removed and the residue was partitioned between water and EtOAc. The EtOAc was separated and washed with brine. Drying (MgSO4), removal of solvent and chromatography on silica gel (100% CH2Cl2 followed by gradient elution to 100% EtOAc and then to 10% MeOH in EtOAc) gave 230 mg of product. MS (ES)(MH+): 470 for C20H25Cl2N5O4; NMR (CDCl3): 1.5 (t, 3H), 2.1 (m, 2H) 2.4 (s, 3H), 3.2 (m, 2H), 3.6 (s, 3H), 3.65 (m, 1H), 4.0 (m, 1H), 4.4 (m, 1H), 4.5 (q, 2H), 7.3 (s, 1H), 8.0 (s, 1H), 9.5 (s, 1H).

Workup

  1. customSolvent was removed
  2. customthe residue was partitioned between water and EtOAc
  3. customThe EtOAc was separated
  4. washwashed with brine
  5. customDrying
  6. custom(MgSO4), removal of solvent and chromatography on silica gel (100% CH2Cl2
  7. washfollowed by gradient elution to 100% EtOAc

Sources & evidence

ORD record
ord-d21986c9aade4a9c84bc05f11ecc8f25
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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