Diisopropylethylamine → HCID 25206447, compound

HRID 387648Notes

Reaction equation

HRID 387648 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=1)[C@H:4]([OH:20])[CH2:5][NH:6][C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH2:9][CH2:8]1.[CH2:30]([O:32][CH2:33][CH2:34][N:35]1[CH2:44][CH2:43][C:42]2[C:41]([C:45](O)=[O:46])=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]1=[O:48])[CH3:31].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>ClCCl>[F:29][C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([F:28])[CH:25]=1)[CH2:21][C@H:3]([NH:2][C:45]([C:41]1[C:42]2[CH2:43][CH2:44][N:35]([CH2:34][CH2:33][O:32][CH2:30][CH3:31])[C:36](=[O:48])[C:37]=2[CH:38]=[CH:39][CH:40]=1)=[O:46])[C@H:4]([OH:20])[CH2:5][NH:6][C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[CH2:9][CH2:8]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68471263HCID 68471263, compoundHCID 86643873HCID 86643873, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 25206447HCID 25206447, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Poured into a suspension of 255 mg of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)butan-2-ol hydrochloride (2:1), 113.5 mg of 2-(2-ethoxyethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid, 9 mg of hydroxybenzotriazole, 104 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 7.6 cm3 of dichloromethane is 0.3 cm3 of N,N-diisopropylethylamine at a temperature close to 20° C. The reaction mixture is kept stirring for 20 h at a temperature close to 20° C. The suspension obtained is filtered and the precipitate is washed once with 5 cm3 of dichloromethane, twice with 5 cm3 of diisopropyl ether, then dried under vacuum. 82 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-2-(2-ethoxyethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are obtained in the form of a white powder.

Workup

  1. customclose to 20° C
  2. customclose to 20° C
  3. customThe suspension obtained
  4. filtrationis filtered
  5. washthe precipitate is washed once with 5 cm3 of dichloromethane, twice with 5 cm3 of diisopropyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-50d05bd739934688bf3de6acd17e3931
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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