Pyridine → HCID 10153489, compound

HRID 1611102Notes

Reaction equation

HRID 1611102 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][O:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=2)=[C:15]1[CH2:36][CH2:37][NH:38][S:39]([CH2:42][C:43]1C=CC=CC=1)(=[O:41])=[O:40])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.N1C=CC=CC=1.[CH3:62][N:63]1C=C(S(Cl)(=O)=O)[N:65]=[CH:64]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO.C(Cl)Cl>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:34][CH:35]=2)=[C:15]1[CH2:36][CH2:37][NH:38][S:39]([C:42]1[N:65]=[CH:64][N:63]([CH3:62])[CH:43]=1)(=[O:40])=[O:41])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 9874688HCID 9874688, compound

Product 1

HCID 10153489HCID 10153489, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (Step 6, Example 1) (1.0 equiv) and Et3N (3.0 equiv) or pyridine (3.0 equiv) in CH2Cl2 (0.05 M) was added 1-methylimidazole-4-sulfonyl chloride (1.2 equiv). The reaction was monitored by TLC (10% MeOH—CH2Cl2) and was heated if necessary. After 30 min the mixture was poured into saturated sodium bicarbonate and extracted with CH2Cl2. The combined organic phase was washed with brine, dried over sodium sulfate and purified by column chromatography to afford 92% of the desired product.

Workup

  1. temperaturewas heated if necessary
  2. extractionextracted with CH2Cl2
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-5ba5e18b5e934c1889e8dd78ffbd3c0a
Source dataset
uspto-grants-2006_01
Patent number
US06984735B2

Reaction notes

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