Diisopropylethylamine → [5-({[1-(4-Hydroxymethyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 928393ノート

反応式

HRID 928393 の反応式
[OH:1][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[C:18]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([CH2:32][NH2:33])=[C:27]([CH3:34])[N:26]=1)([CH3:21])([CH3:20])[CH3:19].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:18]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([CH2:32][NH:33][C:13]([C:11]2[CH:10]=[N:9][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:17][CH:16]=3)[CH:12]=2)=[O:15])=[C:27]([CH3:34])[N:26]=1)([CH3:21])([CH3:20])[CH3:19]

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 580812341-(4-Hydroxymethyl-benzyl)-1H-pyrazole-4-carboxylic acid

生成物 1

HCID 58081225[5-({[1-(4-Hydroxymethyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-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-Hydroxymethyl-benzyl)-1H-pyrazole-4-carboxylic acid (220 mg, 0.95 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (238 mg, 0.95 mmol), HATU (7206 mg, 1.90 mmol) and DIPEA (0.64 mL, 2.84 mmol) in 5 mL DMF was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, dissolved in ethylacetate and extracted with aq. NaHCO3-solution. The organic layer was dried over MgSO4 and evaporated. 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 40ml/min). LCMS (method A) RtA=1.243 min; [M+H]+=466.0.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in ethylacetate
  3. extractionextracted with aq. NaHCO3-solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. 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 40ml/min)
  7. customLCMS (method A) RtA=1.243 min

出典と根拠

ORDレコード
ord-6ec01de6f63e4e4588f4e8ce846288fe
出典データセット
uspto-grants-2016_03
特許番号
US09290485B2

反応ノート

読み込み中…