Diisopropylethylamine → HCID 11951297, compound

HRID 1766446Notes

Reaction equation

HRID 1766446 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([O:18][CH2:19][CH2:20][CH3:21])=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[OH:51].CCN(C(C)C)C(C)C>C(O)(=O)C.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([O:18][CH2:19][CH2:20][CH3:21])=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([NH:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[OH:51])=[O:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21109700HCID 21109700, compound

Product 1

HCID 11951297HCID 11951297, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 23.5 mg (0.072 mmol) 5-(2,4-dichloro-phenyl)-6-propoxy-nicotinic acid, 29 mg (0.09 mmol) TBTU, 10 mg (0.086 mmol) (1R,2R)-2-amino-cyclohexanol and 47.8 mg (0.37 mmol) DIPEA in 1 DMF was shaken at room temperature over night. Acetic acid was added and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/HCOOH. The combined product fractions were evaporated to yield 24.9 mg (85%) of the title compound. MS (m/e): 423.2 (MH+).

Workup

  1. custompurified by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile/water/HCOOH
  4. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-5e3aac54fb884e5c8b533024d5614b94
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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