Triethylamine → HCID 59565293, 화합물

HRID 1962885노트

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HRID 1962885 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 59565293HCID 59565293, 화합물

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6385Tert-Butylamine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6f4b6c90448d43878ad4cb0bda834a24
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415272B2

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