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

HRID 645505노트

반응식

HRID 645505 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2787721603d847e6b5d2429726bde3d0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704996B2

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