Sodium Iodide → N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-phenyl-propionamide

HRID 1697011Notes

Reaction equation

HRID 1697011 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=CN2)=[C:4](NCC(C2C=CC=CC=2)C2C=CC=CC=2)N=1.Cl[C:27]1[N:35]=[C:34]2[C:30]([N:31]=[CH:32][N:33]2[C@@H:36]2[CH2:40][C@H:39]([NH:41][C:42](=[O:51])[CH2:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C@@H:38]([OH:52])[C@H:37]2[OH:53])=[C:29]([NH:54][CH2:55][CH:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[N:28]=1.N1CC[C@@H](N)C1.[I-].[Na+].N[C@@H]1CCN(C2N=C3C(N=CN3[C@@H]3C[C@H](NC(=O)CC4C=CC=CC=4)[C@@H](O)[C@H]3O)=C(NCC(C3C=CC=CC=3)C3C=CC=CC=3)N=2)C1>>[NH2:6][C@@H:5]1[CH2:4][CH2:2][N:10]([C:27]2[N:35]=[C:34]3[C:30]([N:31]=[CH:32][N:33]3[C@@H:36]3[CH2:40][C@H:39]([NH:41][C:42](=[O:51])[CH2:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C@@H:38]([OH:52])[C@H:37]3[OH:53])=[C:29]([NH:54][CH2:55][CH:56]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[N:28]=2)[CH2:9]1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 1519352(3R)-pyrrolidin-3-amineHCID 67019318N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-phenyl-acetamideHCID 86622646N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-phenyl-propionamideHCID 178478404HCID 178478404, compound

Product 1

HCID 67019344N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-phenyl-propionamide

Procedure

The title compound is prepared using a method that is analogous to that used to prepare the compound of Example 22 using N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-phenyl-propionamide, (R)-pyrrolidin-3-ylamine (34 mg, 0.4 mmol) and sodium iodide (6 mg, 0.04 mmol) to give a mixture of two regioisomers which are purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA) to give a product which is predominantly N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-phenyl-acetamide. LCMS (electrospray): m/z [MH+] 647.47

Workup

  1. customto give
  2. additiona mixture of two regioisomers which
  3. customare purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA)
  4. customto give a product which

Sources & evidence

ORD record
ord-6835b214f23445e7a1e682a7c50daa54
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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