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Hydrochloric Acid → 2-[2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]-N-Methylacetamide

HRID 2415545
ノート
印刷プレビュー

反応式

HRID 2415545 の反応式
[CH:1]([N:4](CC)C(C)C)(C)C.[C:10]([N:14]1[CH2:18][C@@H:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[C@H:16]([C:27]([N:29]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=3[CH2:42][C:43](O)=[O:44])[CH2:31][CH2:30]2)=[O:28])[CH2:15]1)([CH3:13])([CH3:12])[CH3:11].CN.Cl.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:10]([N:14]1[CH2:18][C@@H:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[C@H:16]([C:27]([N:29]2[CH2:30][CH2:31][CH:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=3[CH2:42][C:43]([NH:4][CH3:1])=[O:44])[CH2:33][CH2:34]2)=[O:28])[CH2:15]1)([CH3:12])([CH3:11])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69717242[2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]Acetic Acid

生成物 1

HCID 693623392-[2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]-N-Methylacetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N,N-diisopropylethylamine (0.166 mL, 0.953 mmol) was added to a stirred suspension of [2-(1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-5-chlorophenyl]acetic acid (1-10) (40.0 mg), methylamine.HCl (42.9 mg, 0.635 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (48.3 mg, 0.127 mmol) and 1-hydroxy-7-azabenotriazole (17.3 mg, 0.127 mmol) in N,N-dimethylformamide (0.65 mL) at ambient temperature. After approximately 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the residue by preparative reversed phase high pressure liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 0%-100% acetonitrile/water as eluent, 0.1% TFA modifier) gave 1-11 as a buff white solid (m/z (ES) 532 (MH+).

後処理

  1. customat ambient temperature
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by preparative reversed phase high pressure liquid chromatography on YMC Pack Pro
  7. washC18 phase (gradient elution; 0%-100% acetonitrile/water as eluent, 0.1% TFA modifier)

出典と根拠

ORDレコード
ord-8d30d2dcf2144b6f998866b2a366a5e9
出典データセット
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06818658B2

反応ノート

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