Hydrochloric Acid → HCID 22718141, compound

HRID 1582573Notes

Reaction equation

HRID 1582573 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6](C(O)=O)[CH2:5][CH2:4]1.CN(C)CCCN=C=NCC.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:41][C:42]1[C:50]([NH2:51])=[CH:49][CH:48]=[CH:47][C:43]=1[C:44]([NH2:46])=[O:45]>O1CCCC1.O>[NH2:41][C:42]1[C:50]([NH:51][CH:6]2[CH2:7][CH2:8][CH:3]([O:2][CH3:1])[CH2:4][CH2:5]2)=[CH:49][CH:48]=[CH:47][C:43]=1[C:44]([NH2:46])=[O:45]

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 736153Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acidHCID 104870292,3-Diaminobenzamide

Product 1

HCID 22718141HCID 22718141, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g (8.9 mmol) of 4-methoxycyclohexanecarboxylic acid were dissolved in 30 ml of tetrahydrofuran and, at 0° C., successively 1.9 g (1.8 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide×hydrochloride, 1.8 g (11.6 mmol) of N-hydroxybenzotriazole and 1.95 g (19.2 mmol) of triethylamine were added. The mixture was stirred for 1 hour. Then 2.0 g (8.9 mmol) of 2,3-diaminobenzamide×2 hydrochloride and 1.95 g (19.2 mmol) of triethylamine were added. The mixture was then stirred at 0° C. for 1 hour and at room temperature for 16 hours. The mixture was diluted with a large amount of water and extracted several times with ethyl acetate. The organic phases were combined, dried and concentrated in vacuo. 1.5 g of the product were obtained.

Workup

  1. stirringThe mixture was then stirred at 0° C. for 1 hour and at room temperature for 16 hours
  2. extractionextracted several times with ethyl acetate
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae7aaf71cf974d31b4f7d7c10e9f979d
Source dataset
uspto-grants-2004_05
Patent number
US06737421B1

Reaction notes

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