Hydrochloric Acid → {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid

HRID 1159144노트

반응식

HRID 1159144 반응식
C([O:3][C:4](=[O:29])[CH2:5][S:6][C:7]1[N:8]=[C:9]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=3)[N:17]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:16]=2)=[O:14])[S:10][CH:11]=1)C.[OH-].[Na+].Cl>CCO>[CH:26]1([CH2:25][N:17]2[C:18]3[C:23](=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[C:15]([C:13]([NH:12][C:9]3[S:10][CH:11]=[C:7]([S:6][CH2:5][C:4]([OH:29])=[O:3])[N:8]=3)=[O:14])=[CH:16]2)[CH2:28][CH2:27]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86610211HCID 86610211, 화합물

생성물 1

HCID 86610210{2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid수율 83.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

Following general procedure A using 6-fluoroindole and R5X=cyclopropyl-methylbromide {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid ethyl ester was obtained. Ester hydrolysis: 110 mg (0.25 mmol) {2-[(1-cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid ethyl ester was dissolved in EtOH (3 mL) and NaOH (254 μL, 4N) was introduced. The mixture was heated to 80° C. for 1 hour before it was cooled to room temperature and pH was adjusted to 2 using 1 N HCl, where-upon a white precipitate was formed. The product was filtered off and dried to give 85 mg {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid.

후처리

  1. temperaturewas cooled to room temperature
  2. customwas formed
  3. filtrationThe product was filtered off
  4. customdried

출처 및 근거

ORD 기록
ord-84425b85c25a484e9be7a2622abfcba5
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812043B2

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