1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86691760、化合物

HRID 1426988

反応式

HRID 1426988 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 86691760HCID 86691760、化合物収率 105%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b7f18fc37b744e648aff6357e3443e98
出典データセット
uspto-grants-2015_01
特許番号
US08933084B2

関連ノート

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