Triethylamine → HCID 67165929, compound

HRID 1021439Notes

Reaction equation

HRID 1021439 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.O1C2C(=CC=CC=2)CCC1.Cl.[CH3:61][O:62][C:63]1[CH:64]=[C:65]2[C:70](=[CH:71][CH:72]=1)[CH2:69][CH:68]([NH2:73])[CH2:67][CH2:66]2.C(N(CC)CC)C>ClCCCl>[CH3:61][O:62][C:63]1[CH:64]=[C:65]2[C:70](=[CH:71][CH:72]=1)[CH2:69][CH:68]([NH:73][C:18]([C:17]1[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:7][CH2:8][O:9]4)=[CH:4][C:3]=3[C:1]#[N:2])=[CH:22][CH:21]=1)=[O:19])[CH2:67][CH2:66]2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acidHCID 67080381HCID 67080381, compound

Product 1

HCID 67165929HCID 67165929, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of 4-(6-cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid (Preparation 2) (0.0297 g, 0.0841 mmol), 1-(3-(dimethylamino)propyl)-3-ethyl-carbodiimide hydrochloride (0.0177 g, 0.0925 mmol), 1-hydroxybenzotriazole monohydrate (0.0142 g, 0.0925 mmol), and 1,2-dichloroethane (1 ml) was stirred at ambient temperature for 20 minutes. A mixture of chroman-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride (0.0197 g, 0.0924 mmol), triethylamine (0.0585 ml, 0.4203 mmol)), and 1,2-dichloroethane (1 ml) was added to the activated acid and the mixture was stirred for 17 hours at ambient temperature. The crude mixture was purified on silica gel (MeOH in dichloromethane gradient) to provide 29.5 mg of the title compound as a foamy film (69%)

Workup

  1. additionwas added to the activated acid
  2. stirringthe mixture was stirred for 17 hours at ambient temperature
  3. customThe crude mixture was purified on silica gel (MeOH in dichloromethane gradient)

Sources & evidence

ORD record
ord-f8a9b11c3ffb49ccaf5dc259e9d62b66
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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