Triethylamine → HCID 59565293, compound

HRID 1962885Notes

Reaction equation

HRID 1962885 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([OH:17])=O)=[C:8]([F:20])[C:7]=2[CH3:21])#[CH:2].CN(C(ON1N=[N:37][C:32]2[CH:33]=CC=C[C:31]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:44]CN(CC)CC.[NH4+].[Cl-]>CC#N.C(N)(C)(C)C>[C:32]([NH:37][C:15](=[O:17])[CH:14]([O:13][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([CH3:21])[C:8]=1[F:20])[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]2)[S:18][CH3:19])([CH3:44])([CH3:33])[CH3:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86647256HCID 86647256, compound

Product 1

HCID 59565293HCID 59565293, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6385Tert-ButylamineSolvent

Procedure

To a mixture containing (3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (250 mg) from Step 8, aza-HOBT (116 mg), TBTU (273 mg) and Et3N (0.32 ml) in CH3CN (12 ml), tert-butyl amine was added at room temperature, under a nitrogen atmosphere. The resulting brown suspension was stirred 1 hour at room temperature then poured into aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate) to give N-tert-butyl-2-(3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (201 mg) as white solid. 1H NMR (CDCl3) δ ppm: 8.88 (1H, d); 8.17 1H, d); 7.17 (1H, d); 6.64 (1H, br s); 5.59 (1H, s); 3.27 (1H, s); 2.69 (3H, d); 2.18 (3H, s); 1.44 (9H, s).

Workup

  1. additionwas added at room temperature, under a nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate anhydrous
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-6f4b6c90448d43878ad4cb0bda834a24
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

Loading…