Triethylamine → HCID 90241885, compound

HRID 2202035Notes

Reaction equation

HRID 2202035 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[NH2:42][CH2:43][CH:44]([OH:56])[CH2:45][N:46]1[CH2:55][CH2:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:47]1>C(Cl)Cl>[CH2:47]1[C:48]2[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:54][CH2:55][N:46]1[CH2:45][CH:44]([OH:56])[CH2:43][NH:42][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[CH3:1]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 160962-Methyl-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

Product 1

HCID 90241885HCID 90241885, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-methyl-3-nitrobenzoic acid (1.0 g, 5.5 mmol) in DCM (20 mL) was added EDCI (1.58 g, 8.25 mmol), HOBt (1.11 g, 8.25 mmol), Et3N (1.11 g, 11.0 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (1.36 g, 6.6 mmol). The mixture was stirred at 25° C. for 16 h. The reaction solution was washed with water and extracted with DCM. The organic layer was concentrated, and the residue was purified by column chromatography to give the title product (1.6 g, 78.8%). LCMS (m/z): 370.2 (M+1).

Workup

  1. washThe reaction solution was washed with water
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b9bfdccbf0df42cbbf789ce904fe35bf
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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