Triethylamine → HCID 44514434, compound

HRID 1011641Notes

Reaction equation

HRID 1011641 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1([C:26]2[NH:27][C:28]3[C:33]([C:34]=2[CH3:35])=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18][CH2:17][C:16]([N:23]([CH3:25])[CH3:24])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:14]1.C(N(CC)CC)C.[CH:43]1([S:48](Cl)(=[O:50])=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44]1.[OH-].[Na+]>ClCCl>[CH2:19]([C:16]1([N:23]([CH3:25])[CH3:24])[CH2:17][CH2:18][C:13]([C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH2:3][CH2:2][NH:1][S:48]([CH:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)(=[O:50])=[O:49])=[CH:11][CH:10]=[CH:9][CH:8]=3)([C:26]2[NH:27][C:28]3[C:33]([C:34]=2[CH3:35])=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:14][CH2:15]1)[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 3717197Cyclopentanesulfonyl chlorideHCID 44514152HCID 44514152, compound

Product 1

HCID 44514434HCID 44514434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-(2-aminoethyl)-1H-indol-2-yl)-1-butyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexylamine (120 mg, 0.255 mmol, mixture of the two possible diastereoisomers in a ratio of approx. 30:70) mixed in dichloromethane (5 ml) with triethylamine (0.12 ml, 0.863 mmol) and cyclopentane sulphonyl chloride (65 mg, 0.385 mmol). After a reaction time of 24 h at 25° C. the reaction mixture was mixed with 1N sodium hydroxide solution (10 ml) and extracted with dichloromethane (3×15 ml). The combined organic phases were dried with Na2SO4 and then filtered. The volatile constituents of the filtrate were completely removed in a vacuum. The residue (yellow foam, 173 mg) was purified by column chromatography [silica gel 60 (25 g); ethyl acetate/methanol 4:1 (250 ml), methanol/30% ammonia 9:1 (100 ml)]. The product was obtained as a beige-coloured solid with a yield of 39 mg (25%) (melting point 111-115° C., AS 11227, mixture of the two possible diastereoisomers in a ratio of approx. 30:70).

Workup

  1. extractionextracted with dichloromethane (3×15 ml)
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. filtrationfiltered
  4. customThe volatile constituents of the filtrate were completely removed in a vacuum
  5. customThe residue (yellow foam, 173 mg) was purified by column chromatography [silica gel 60 (25 g); ethyl acetate/methanol 4:1 (250 ml), methanol/30% ammonia 9:1 (100 ml)]
  6. customThe product was obtained as a beige-coloured solid with a yield of 39 mg (25%) (melting point 111-115° C.
  7. additionAS 11227, mixture of the two possible diastereoisomers in a ratio of approx. 30:70)

Sources & evidence

ORD record
ord-f14e4c4a24684747a64da84554b6d34c
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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