Diisopropylethylamine → (S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

HRID 737177노트

반응식

HRID 737177 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:49][C:50]1[S:51][CH:52]=[C:53]([C:55]2[CH:66]=[CH:65][C:58]([C:59]([NH:61][CH:62]3[CH2:64][CH2:63]3)=[O:60])=[CH:57][CH:56]=2)[N:54]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][C@H:9]1[C:13](=[O:15])[NH:49][C:50]1[S:51][CH:52]=[C:53]([C:55]2[CH:56]=[CH:57][C:58]([C:59](=[O:60])[NH:61][CH:62]3[CH2:64][CH2:63]3)=[CH:65][CH:66]=2)[N:54]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14775612(S)-3-Boc-thiazolidine-2-carboxylic acidHCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

생성물 1

HCID 57849787(S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-Thiazolidine-2,3-dicarboxylic acid 3-tert-butyl ester (49.4 mg, 0.21 mmol) was dissolved in DMF (2 mL). DIEA (74 μL, 0.42 mmol) was added followed by HATU (80.7 mg, 0.21 mmol). The reaction was stirred at ambient temperature for 15 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide (54.6 mg, 0.21 mmol) was added. The reaction was stirred at ambient temperature overnight and then heated to 50° C. for 7 hours. The reaction was cooled, filtered, and purified by reverse phase HPLC to give the desired product. Yield 30.5 mg. MS: 475.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.54-0.75 (m, 4H), 1.22-1.47 (m, 9H), 2.79-2.90 (m, 1H), 3.05-3.25 (m, 2H), 3.55-3.75 (m, 1H), 5.33-5.50 (m, 2H), 7.78-7.98 (m, 5H), 8.40-8.48 (d, 1H), 12.50-12.59 (s, 1H).

후처리

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. temperatureheated to 50° C. for 7 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-177bd830eebe4d178d796954300526e4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595398B2

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