1-Methyl-1H-pyrrole-3-sulfonyl chloride → HCID 57467273, compound

HRID 1044529Notes

Reaction equation

HRID 1044529 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][NH2:19])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.[CH3:28][N:29]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30]1>ClCCl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][NH:19][S:34]([C:31]3[CH:32]=[CH:33][N:29]([CH3:28])[CH:30]=3)(=[O:36])=[O:35])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 220658921-Methyl-1H-pyrrole-3-sulfonyl chlorideHCID 57471427HCID 57471427, compound

Product 1

HCID 57467273HCID 57467273, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-(8-(3-Fluorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yloxy)ethanamine (50 mg, 0.136 mmol) was dissolved in dichloromethane (2 mL). N,N-Dimethyl-4-aminopyridine (49.7 mg, 0.407 mmol) and 1-methyl-1H-pyrrole-3-sulfonyl chloride (24.4 mg, 0.136 mmol) were added successively. The reaction mixture was stirred at room temperature over night. The reaction was diluted with dichloromethane and washed with water. The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 31 mg (0.061 mmol, 45%).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent was evaporated in vacuo
  4. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record
ord-fd6880e1f4f649fb923201c6205a02bf
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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