1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86691760, 화합물

HRID 1426988

반응식

HRID 1426988 반응식
[F:1][C:2]1([F:27])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[CH:14][C:15]([C:16](O)=[O:17])=[C:9]3[N:8]=2)[CH:4]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[OH:26])[CH2:3]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:50][CH2:51][C@H:52]([OH:55])[CH2:53][Cl:54].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:54][CH2:53][C@@H:52]([OH:55])[CH2:51][NH:50][C:16]([C:15]1[CH:14]=[N:13][N:10]2[CH:11]=[CH:12][C:7]([N:5]3[CH2:6][C:2]([F:1])([F:27])[CH2:3][CH:4]3[C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[OH:26])=[N:8][C:9]=12)=[O:17]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1350101-Amino-3-chloro-2-propanol hydrochloride, (S)-HCID 67470704HCID 67470704, 화합물

생성물 1

HCID 86691760HCID 86691760, 화합물수율 105%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 5-(4,4-difluoro-2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.047 g, 0.124 mmol) and HOBT (0.0252 g, 0.186 mmol) in DMF (1 mL) at ambient temperature was added EDCI (0.0357 g, 0.186 mmol). The resulting mixture was stirred for 1 hour. To this mixture was added (S)-1-amino-3-chloropropan-2-ol hydrochloride (Example 19, Step A; 0.0218 g, 0.149 mmol) followed by DIEA (0.0656 mL, 0.373 mmol) at ambient temperature. The resulting mixture was stirred for 48 hours. The reaction mixture was diluted with EtOAc (10 mL), and the organic layer was washed with a 1:1 mixture of brine and water. The aqueous layer was separated and extracted with EtOAc (2×10 mL). The combined organic layers were washed with a 1:1 mixture of brine and water (15 mL) and combined with the organic layer obtained previously. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to afford N-((S)-3-chloro-2-hydroxypropyl)-5-(4,4-difluoro-2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (0.061 g, 105% yield). LC/MS (ES+APCI) m/z=468.1 (M−H).

후처리

  1. stirringThe resulting mixture was stirred for 48 hours
  2. washthe organic layer was washed with a 1:1 mixture of brine and water
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (2×10 mL)
  5. washThe combined organic layers were washed with a 1:1 mixture of brine and water (15 mL)
  6. customobtained previously
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b7f18fc37b744e648aff6357e3443e98
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933084B2

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