Triethylamine → HCID 10228153, compound

HRID 1825005Notes

Reaction equation

HRID 1825005 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[F:19])[C:6]([C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1)=[O:21])=[CH:5]2.C(N(CC)CC)C.[CH3:37][C:38]([CH3:44])([CH3:43])[CH2:39][C:40](Cl)=[O:41]>ClCCl>[F:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([F:19])[C:12]=1[CH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:40](=[O:41])[CH2:39][C:38]([CH3:44])([CH3:43])[CH3:37])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 11361321HCID 11361321, compound

Product 1

HCID 10228153HCID 10228153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

59 mg (0.150 mmol) of the compound from Example XIV and 0.04 ml (0.30 mmol) of triethylamine are initially-charged in 5 ml of dichloromethane. At 0° C., a solution of 26 mg of 3,3-dimethylbutyryl chloride (0.195 mmol) in 1 ml of dichloromethane is added dropwise, and the mixture is stirred at RT for 30 min. The reaction solution is concentrated and the residue is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane→cyclohexane:ethyl acetate 2.5:1). The resulting product is taken up in a little ethyl acetate, precipitated by addition of n-pentane, filtered off with suction and dried. This gives 35 mg (45% of theory) of a light-beige solid.

Workup

  1. concentrationThe reaction solution is concentrated
  2. customthe residue is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane→cyclohexane:ethyl acetate 2.5:1)
  3. customprecipitated by addition of n-pentane
  4. filtrationfiltered off with suction
  5. customdried

Sources & evidence

ORD record
ord-a0dd689787f7498fa7b1696c69ed5781
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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