Triethylamine → HCID 46213752, compound

HRID 1092548Notes

Reaction equation

HRID 1092548 reaction equation
CC(C)C(C1C=CC=CC=1)C([NH:6][C@@H:7]1[C@H:14]2[C@H:10]([CH2:11][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[CH2:13]2)[CH2:9][CH2:8]1)=O.C(N(CC)CC)C.[F:40][C:41]([F:53])([F:52])[C:42]1[CH:43]=[C:44]([S:48](Cl)(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=1>ClCCl>[F:40][C:41]([F:53])([F:52])[C:42]1[CH:43]=[C:44]([S:48]([NH:6][C@@H:7]2[C@H:14]3[C@H:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=4)[CH2:13]3)[CH2:9][CH2:8]2)(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 665909373-methyl-2-phenyl-N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}butanamide

Product 1

HCID 46213752HCID 46213752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3aS*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 122 Step E (200 mg, 0.703 mmol) in dichloromethane (2 mL) was added triethylamine (0.147 mL, 1.055 mmol) followed by 3-(trifluoromethyl)benzene-1-sulfonyl chloride (0.124 mL, 0.774 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with water and extracted with dichloromethane. The organics were reduced in volume and loaded onto a silica gel cartridge (Analogix®, Burlington, Wis., RS-24). The title compounds were eluted with a gradient of 0% to 10% methanol (2 N ammonia)/dichloromethane over 20 minutes.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe title compounds were eluted with a gradient of 0% to 10% methanol (2 N ammonia)/dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-d36006090e254e16ba20af182cba9ba6
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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