Triethylamine → HCID 67287501, compound

HRID 1626417Notes

Reaction equation

HRID 1626417 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]([OH:20])=O)=[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.Cl.Cl.[F:52][C:53]([F:64])([F:63])[C:54]1[CH:55]=[CH:56][C:57]([CH2:60][CH2:61][NH2:62])=[N:58][CH:59]=1.C(N(CC)CC)C>ClCCCl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18](=[O:20])[NH:62][CH2:61][CH2:60][C:57]3[CH:56]=[CH:55][C:54]([C:53]([F:64])([F:52])[F:63])=[CH:59][N:58]=3)=[CH:21][CH:22]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N: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 53407548HCID 53407548, compound

Product 1

HCID 67287501HCID 67287501, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (20 mg, 0.0566 mmol), 1-(3-(dimethylamino)propyl)-3-ethyl-carbodiimide hydrochloride (12.85 mg, 0.0670 mmol), 1-hydroxybenzotriazole monohydrate (10.26 mg, 0.0670 mmol), and 1,2-dichloroethane (1 mL) was stirred at ambient temperature for 20 minutes. 2-(5-(Trifluoromethyl)pyridin-2-yl)ethanamine dihydrochloride (19.23 mg, 0.0731 mmol) and triethylamine (84.91 μl, 0.6092 mmol) were added to the activated acid and the mixture was stirred for 18 hours at ambient temperature. The reaction mixture was purified on silica gel (MeOH in dichloromethane gradient) to provide 14.2 mg of the title compound as a thin film (48%).

Workup

  1. stirringthe mixture was stirred for 18 hours at ambient temperature
  2. customThe reaction mixture was purified on silica gel (MeOH in dichloromethane gradient)

Sources & evidence

ORD record
ord-f3a27845b90743f088511fd907af4ba4
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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