HOAt → (r)-2-Cyano-4-(methylspiro[2.5]oct-6-ylmethylamino)pyrimidine-5-carboxylic acid (2-phenyl-1-pyrrolidin-1-ylmethylethyl)amide

HRID 645505ノート

反応式

HRID 645505 の反応式
[C:1]([C:3]1[N:8]=[C:7]([N:9]([CH3:19])[CH2:10][CH:11]2[CH2:18][CH2:17][C:14]3([CH2:16][CH2:15]3)[CH2:13][CH2:12]2)[C:6]([C:20](O)=[O:21])=[CH:5][N:4]=1)#[N:2].[C:23]1([CH2:29][C@@H:30]([NH2:37])[CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[C:23]1([CH2:29][C@@H:30]([NH:37][C:20]([C:6]2[C:7]([N:9]([CH3:19])[CH2:10][CH:11]3[CH2:18][CH2:17][C:14]4([CH2:15][CH2:16]4)[CH2:13][CH2:12]3)=[N:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[O:21])[CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

6

反応物 4

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12184138(r)-2-Phenyl-1-pyrrolidin-1-ylmethylethylamineHCID 687036062-Cyano-4-(methylspiro[2.5]oct-6-ylmethylamino)pyrimidine-5-carboxylic acid

生成物 1

HCID 131728088(r)-2-Cyano-4-(methylspiro[2.5]oct-6-ylmethylamino)pyrimidine-5-carboxylic acid (2-phenyl-1-pyrrolidin-1-ylmethylethyl)amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the crude 2-cyano-4-(methylspiro[2.5]oct-6-ylmethylamino)pyrimidine-5-carboxylic acid (82 mg, step 73.4) in DMF (1.5 mL) are added (R)-2-phenyl-1-pyrrolidin-1-ylmethylethylamine (0.3 mmol), EDCI-HCl (0.4 mmol), and HOAt (0.4 mmol) at room temperature. The reaction mixture is stirred for 24 h and the reaction is quenched by the addition of water. The mixture is extracted with AcOEt and the organic extracts are dried over Na2SO4, filtered, concentrated in vacuo. The resulting residue is purified by RP-HPLC to give the title compound; MS (M+1)+ 488, Rf (solvent) 0.13 (CH2Cl2:MeOH=10:1).

後処理

  1. customthe reaction is quenched by the addition of water
  2. extractionThe mixture is extracted with AcOEt
  3. dry with materialthe organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified by RP-HPLC

出典と根拠

ORDレコード
ord-2787721603d847e6b5d2429726bde3d0
出典データセット
uspto-grants-2010_04
特許番号
US07704996B2

反応ノート

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