Pyridine → HCID 56966133, compound

HRID 1036948Notes

Reaction equation

HRID 1036948 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1.N1C=CC=CC=1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:31]=1.CC1(C)C2C(=CC=C(C)C=2)NC(C2C=C(N)C=CC=2)C1>ClCCl>[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:17]=[C:18]([NH:22][S:36]([C:32]3[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=3)(=[O:38])=[O:37])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamineHCID 672916153-(4,4-Dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966133HCID 56966133, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (150 mg, 0.47 mmol) in pyridine (0.74 mg, 0.94 mmol) and dichloromethane (3 mL) at 0° C. was added dropwise a solution of pyridine-3-sulfonyl chloride (100 mg, 0.56 mmol) in dichloromethane (1 mL). The mixture was stirred at room temperature overnight. Thin layer chromatography and LC-MS indicated that 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine was consumed completely. The mixture was quenched with water (5 mL) and extracted with dichloromethane (5 mL×2). The combined organic layers were dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel to afford pyridine-3-sulfonic acid [3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide (170 mg, 78.7%) as a white solid. MS (ESI+APCI) M+1=442.3.

Workup

  1. customwas consumed completely
  2. customThe mixture was quenched with water (5 mL)
  3. extractionextracted with dichloromethane (5 mL×2)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4a3e5d714849424aa60aef1039e21c39
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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