Dichloromethane → HCID 67178111, compound

HRID 1676959Notes

Reaction equation

HRID 1676959 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[CH2:27][CH2:26][CH2:25][C@H:24]3[CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:22])=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:34][Si](C=[N+]=[N-])(C)C.CCCCCC.[Cl:47]CCl>>[ClH:47].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]([CH3:34])[C:15]2[CH:16]=[CH:17][C:18]([C:21]([N:23]3[CH2:27][CH2:26][CH2:25][C@H:24]3[CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:22])=[CH:19][CH:20]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 15951139HCID 15951139, compound

Product 1

HCID 67178111HCID 67178111, compound

Procedure

To a stirred solution of 4-methanesulfonyl-N-[4-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-benzenesulfonamide (Example 22) (0.028 g, 0.057 mmol) in 2 ml dichloromethane (2 mL) is added 2 M (trimethylsilyl)diazomethane in hexane (0.063 ml, 0.126 mmol) and allowed to react for 5 hours at ambient temperature. The reaction is diluted with dichloromethane and washed with 0.1 N HCl. The organic layer are dried over anhydrous sodium sulfate, filtered, and concentrated to an oily solid. The oily solid is converted to the hydrochloride salt in accordance with the preparation of the title compound of Example 23 (C-Phenyl-N-[4-(2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-methanesulfonamide; hydrochloride) to provide the title compound as a solid. MS (ES+) m/e 506.1 (M+1)+.

Workup

  1. customto react for 5 hours at ambient temperature
  2. washwashed with 0.1 N HCl
  3. dry with materialThe organic layer are dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oily solid
  6. customThe oily solid is converted to the hydrochloride salt in accordance with the preparation of the title compound of Example 23 (C-Phenyl-N-[4-(2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-methanesulfonamide; hydrochloride)

Sources & evidence

ORD record
ord-638d0a6c6bce4ef393983d869c162b27
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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