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

HRID 9921

Reaction equation

HRID 9921 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-070783df20e7489689e0498417256699
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

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