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Triethylamine → tert-butyl (2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)(6-{[(1-methylcyclopropyl)carbonyl]amino}pyridin-3-yl)carbamate

HRID 1039079
ノート
印刷プレビュー

反応式

HRID 1039079 の反応式
NC1C(C)=CC([N:8]([CH2:16][CH2:17][C@@H:18]2[CH2:20][C@@H:19]2[CH:21]2[CH2:26][CH2:25][N:24]([C:27]3[N:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=3)[CH2:23][CH2:22]2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=NC=1.[CH3:35][C:36]1([C:39]([OH:41])=O)[CH2:38][CH2:37]1.CN(C(O[N:50]1N=N[C:52]2[CH:53]=[CH:54][CH:55]=[N:56][C:51]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:33][C:30]1[CH:31]=[N:32][C:27]([N:24]2[CH2:23][CH2:22][CH:21]([C@H:19]3[CH2:20][C@H:18]3[CH2:17][CH2:16][N:8]([C:54]3[CH:55]=[N:56][C:51]([NH:50][C:39]([C:36]4([CH3:35])[CH2:38][CH2:37]4)=[O:41])=[CH:52][CH:53]=3)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:26][CH2:25]2)=[N:28][CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 813261-Methylcyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67962339tert-butyl (5-amino-4-methylpyridin-2-yl)(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)carbamate

生成物 1

HCID 86666144
tert-butyl (2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)(6-{[(1-methylcyclopropyl)carbonyl]amino}pyridin-3-yl)carbamate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

tert-butyl (5-amino-4-methylpyridin-2-yl)(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)carbamate (80 mg, 0.17 mmol) from Step 2 of Example 30a, 1-methylcyclopropane-1-carboxylic acid (19.2 mg, 0.19 mmol), HATU (84 mg, 0.22 mmol) and triethylamine (68.5 mg, 0.68 mmol) were added in DMF (1.7 mL) at room temperature for 2 days. The reaction was added ethyl acetate (20 mL, washed with sodium bicarbonate saturated solution (10 mL), second wash with brine (10 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 30% ethyl acetate/hexanes to give the title compound as a pale yellow oil.

後処理

  1. washwashed with sodium bicarbonate saturated solution (10 mL)
  2. washsecond wash with brine (10 mL)
  3. dry with materialThe organic phase was dried by magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge
  7. washeluting with 30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-64211d634c044e25816265ca9af82ce7
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08552022B2

反応ノート

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