Triethylamine → HCID 131726695, compound

HRID 1594349Notes

Reaction equation

HRID 1594349 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[OH:22])=[CH:17][CH2:16]2)=[CH:10][CH:9]=1.[F:33][C:34]1[CH:35]=[C:36]([N:41]=[C:42]=[O:43])[CH:37]=[C:38]([F:40])[CH:39]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:33][C:34]1[CH:35]=[C:36]([NH:41][C:42]([O:22][CH:21]([C:18]2[CH2:19][CH2:20][N:15]([CH2:14][C:11]3[CH:12]=[CH:13][C:8]([O:7][C:2]4[N:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:9][CH:10]=3)[CH2:16][CH:17]=2)[C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)=[O:43])[CH:37]=[C:38]([F:40])[CH:39]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27792821,3-Difluoro-5-isocyanatobenzeneHCID 68681649HCID 68681649, compound

Product 1

HCID 131726695HCID 131726695, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared in a manner analogous to that of Step F of Example 2, using 0.44 gram (0.0010 mole) of {1-[(4-pyrimidin-2-yloxyphenyl)methyl](4-1,2,5,6-tetrahydropyridyl)}[4-(trifluoromethyl)phenyl]methanol, 0.21 gram (0.0014 mole) of 3,5-difluorophenylisocyanate, 0.14 gram (0.0014 mole) of triethylamine, and 0.05 gram (catalyst) of 4-dimethylaminopyridine in 15 mL of methylene chloride. The reaction product was purified with column chromatography on silica gel using 10% to 25% acetone/methylene chloride mixtures as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.18 gram of Compound 786, mp 85–92° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step F of Example 2
  2. customThe reaction product was purified with column chromatography on silica gel using 10% to 25% acetone/methylene chloride mixtures as eluants
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff052da763df4cb69f437788a5dfaa64
Source dataset
uspto-grants-2007_11
Patent number
US07300946B2

Reaction notes

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