Tryptamine → HCID 178505055, compound

HRID 272251

Reaction equation

HRID 272251 reaction equation
[CH2:1]([N:8]([CH2:24][C@H:25]([OH:47])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:30]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:29]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[NH2:69][CH2:70][CH2:71][C:72]1[C:80]2[C:75](=[CH:76][CH:77]=[CH:78][CH:79]=2)[NH:74][CH:73]=1>ClCCl.C(#N)C.C(N(CC)CC)C>[CH2:1]([N:8]([CH2:24][C@H:25]([OH:47])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[C:30]([NH:42][S:43]([CH3:46])(=[O:44])=[O:45])[CH:29]=1)[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH:69][CH2:70][CH2:71][C:72]3[C:80]4[C:75](=[CH:76][CH:77]=[CH:78][CH:79]=4)[NH:74][CH:73]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1150TryptamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178505057HCID 178505057, compound

Product 1

HCID 178505055HCID 178505055, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 0.3 g (0.45 mmol) of trans-4-[4-(benzyl{(2S)-3-[4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy]-2-hydroxypropyl}amino)cyclohexyl]benzoic acid (preparation 3), of 0.78 g (0.91 mmol) of 1-hydroxybenzotriazole, of 0.175 g (0.91 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, of 0.19 ml of triethylamine and of 0.138 g (0.86 mmol) of tryptamine in a mixture of 4 ml of dichloromethane and 0.8 ml of acetonitrile is stirred for 24 h. The solvents are evaporated under reduced pressure. Dichloromethane and water are added and the organic phase is washed three times with water. The organic phases are dried over magnesium sulfate and concentrated under reduced pressure. The title compound is obtained in the form of a white solid (0.246 g, 58%) after purification on silica gel (eluent: heptane/ethyl acetate 60/40 for 10 min, 60/40 to 40/60 in 10 min and then 40/60 for 20 min gradient). [M+H+]=801.6

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. additionDichloromethane and water are added
  3. washthe organic phase is washed three times with water
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea988d814a9d4954a72630fd61008ae2
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Linked notes

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