Methanesulfonyl chloride → HCID 131730326, compound

HRID 1948319Notes

Reaction equation

HRID 1948319 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]([N:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:25]([C:27]3[NH:28][C:29]([CH3:34])=[C:30]([Cl:33])[C:31]=3[Cl:32])=[O:26])[C@H:20]([O:35][CH3:36])[CH2:19]2)=[N:9][CH:8]=1>N1C=CC=CC=1>[Cl:32][C:31]1[C:30]([Cl:33])=[C:29]([CH3:34])[NH:28][C:27]=1[C:25]([NH:24][C@H:21]1[CH2:22][CH2:23][N:18]([C:10]2[CH:11]=[C:12]([C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][N:9]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:19][C@H:20]1[O:35][CH3:36])=[O:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 131730323HCID 131730323, compound

Product 1

HCID 131730326HCID 131730326, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (16 μl, 21 mmol) was added to 66 mg (0.14 mmol) of Cis(±)-ethyl 5-amino-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)isonicotinate (Example 194) in 3 ml pyridine. After stirring for 1 h, 5 μl more methanesulfonyl chloride was added. Stirred at room temperature overnight. Solvent was removed, and the residue was partitioned between EtOAc and Na2CO3 (aqueous). The EtOAc was separated and washed with water and brine. Drying (MgSO4) and removal of solvent gave 63 mg of product. MS (ES)(MH+): 534 for C21H27Cl2N5O6S, NMR (d6-DMSO): 1.4 (t, 3H), 1.8 (m, 2H) 2.2 (s, 3H), 2.9 (s, 3H), 3.1-3.2 (m, 2H), 3.3-3.5 (m), 3.6 (m, 1H), 4.2-4.3 (m, 2H), 4.4 (q, 2H), 4.7 (m, 1H), 7.1 (s, 1H), 7.2 (d, 1H), 8.2 (s, 1H), 12.2 (s, 1H).

Workup

  1. stirringStirred at room temperature overnight
  2. customSolvent was removed
  3. customthe residue was partitioned between EtOAc and Na2CO3 (aqueous)
  4. customThe EtOAc was separated
  5. washwashed with water and brine
  6. customDrying
  7. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-fbeeff6d13404188ada502f82b97fd82
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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