3-Chlorobenzoic Acid → 6-(4-[3-Chloro-benzoyl-amino]-phenyl-amino)-9-ethyl-2-(2-hydroxy-ethyl-amino)-9H-purine

HRID 9921

반응식

HRID 9921 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][OH:21])[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH2:22][CH3:23])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.C(NC(C)C)(C)C.[Cl:68][C:69]1[CH:70]=[C:71]([CH:75]=[CH:76][CH:77]=1)[C:72](O)=[O:73]>CC(N(C)C)=O.C(OCC)(=O)C>[Cl:68][C:69]1[CH:70]=[C:71]([CH:75]=[CH:76][CH:77]=1)[C:72]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][OH:21])[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH2:22][CH3:23])=[CH:4][CH:3]=1)=[O:73]

참가 물질

8

반응물 5

HCID 4473-Chlorobenzoic AcidHCID 7912DiisopropylamineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 219882846-(4-amino-phenyl-amino)-9-ethyl-2-(2-hydroxy-ethyl-amino)-9H-purine

생성물 1

HCID 219882386-(4-[3-Chloro-benzoyl-amino]-phenyl-amino)-9-ethyl-2-(2-hydroxy-ethyl-amino)-9H-purine

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

62 mg (0.2 mmol) of 6-(4-amino-phenyl-amino)-9-ethyl-2-(2-hydroxy-ethyl-amino)-9H-purine (prepared according to Example 108), 0.18 g (0.4 mmol) of (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP), 54 mg (0.4 mmol) of 1-hydroxybenzotriazole (HOBT) and 68 μl of diisopropylamine are stirred in 6 ml of dimethylacetamide at RT for 5 min and then treated with 63 mg (0.4 mmol) of 3-chlorobenzoic acid. After the reaction mixture has been stirred at RT for 30 min, it is diluted with ethyl acetate and washed with water. The crude product is purified by chromatography over silica gel (mobile phase: methylene chloride:methanol=9:1). 6-(4-[3-Chloro-benzoyl-amino]-phenyl-amino)-9-ethyl-2-(2-hydroxy-ethyl-amino)-9H-purine is obtained; FAB-MS: (M+H)+=452; Rf=0.45 (methylene chloride:methanol=9:1).

후처리

  1. washwashed with water
  2. customThe crude product is purified by chromatography over silica gel (mobile phase: methylene chloride:methanol=9:1)

출처 및 근거

ORD 기록
ord-070783df20e7489689e0498417256699
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091346B1

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