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Diisopropylethylamine → [4,6-Dimethyl-5-({[1-(4-pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carbonyl]-amino}-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 928368
ノート
印刷プレビュー

反応式

HRID 928368 の反応式
[N:1]1([CH2:6][C:7]2[CH:21]=[CH:20][C:10]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([OH:19])=O)[N:14]=[CH:13]3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:22]([O:26][C:27](=[O:39])[NH:28][C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([CH2:36][NH2:37])=[C:31]([CH3:38])[N:30]=1)([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:22]([O:26][C:27](=[O:39])[NH:28][C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([CH2:36][NH:37][C:17]([C:15]2[N:14]=[CH:13][N:12]([CH2:11][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][N:1]4[CH:5]=[CH:4][CH:3]=[N:2]4)=[CH:21][CH:20]=3)[CH:16]=2)=[O:19])=[C:31]([CH3:38])[N:30]=1)([CH3:25])([CH3:24])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475372N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamideHCID 580812291-(4-Pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carboxylic acid

生成物 1

HCID 58081281
[4,6-Dimethyl-5-({[1-(4-pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carbonyl]-amino}-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 1-(4-Pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carboxylic acid (0.67 g, 2.4 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.61 g, 2.4 mmol), HATU (1.8 g, 4.8 mmol) and DIPEA (1.3 mL, 7.2 mmol) in 10 mL DMF was stirred at room temperature for 16 h. The mixture was evaporated and the residue was partitioned between ethyl acetate and 1 N aq. HCl. The organic layer was dried over MgSO4 and evaporated in vacuo. The crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min). LCMS (method A) RtA=1.418 min; [M+H]+=516.1.

後処理

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1 N aq. HCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min)
  6. customLCMS (method A) RtA=1.418 min

出典と根拠

ORDレコード
ord-d57da4a786e143dc8a6d5664d54a7769
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290485B2

反応ノート

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