Triethylamine → 5-[Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amino]-pentanoic acid naphthalen-2-ylamide

HRID 1942395Notes

Reaction equation

HRID 1942395 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1)[CH2:2][CH3:3].[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[NH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29]Br.C(N(CC)CC)C>CC(C)=O>[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[NH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amineHCID 669374455-Bromo-pentanoic acid naphthalen-2-ylamide

Product 1

HCID 669374525-[Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amino]-pentanoic acid naphthalen-2-ylamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9 is prepared from 1C and 9A using the same method as for 6 with acetone as solvent and triethylamine as base. Reaction temperature is 50° C. After evaporation of the solvent the residue is suspended in water, alkalized with sodium hydroxide solution and extracted three times with dichloromethane. After evaporation of the combined organic phases the product is crystallized as salt of maleic acid from acetonitrile/diethylether.

Workup

  1. customReaction temperature
  2. customis 50° C
  3. customAfter evaporation of the solvent the residue
  4. extractionextracted three times with dichloromethane
  5. customAfter evaporation of the combined organic phases the product
  6. customis crystallized as salt of maleic acid from acetonitrile/diethylether

Sources & evidence

ORD record
ord-72f48c4767c14a9d8d616a8a90e2683e
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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