Acetyl chloride → N-((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

HRID 1697028Notes

Reaction equation

HRID 1697028 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].N1(C2C=CC=CN=2)CCC(NC(=O)NCCNC(C2N=C3C(N=CN3[C@@H]3C[C@H](NC(=O)C)[C@@H](O)[C@H]3O)=C(NCC(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=O)CC1.[NH2:64][C@@H:65]1[CH2:69][CH2:68][N:67]([C:70]2[N:78]=[C:77]3[C:73]([N:74]=[CH:75][N:76]3[C@@H:79]3[CH2:83][C@H:82]([NH:84][C:85](=[O:88])[CH2:86][CH3:87])[C@@H:81]([OH:89])[C@H:80]3[OH:90])=[C:72]([NH:91][CH2:92][CH:93]([C:100]3[CH:105]=[CH:104][CH:103]=[CH:102][CH:101]=3)[C:94]3[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=3)[N:71]=2)[CH2:66]1.C(Cl)(=O)C.[N:110]([C:113]1[CH:114]=[N:115][CH:116]=[CH:117][CH:118]=1)=[C:111]=[O:112]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:94]1([CH:93]([C:100]2[CH:101]=[CH:102][CH:103]=[CH:104][CH:105]=2)[CH2:92][NH:91][C:72]2[N:71]=[C:70]([N:67]3[CH2:68][CH2:69][C@@H:65]([NH:64][C:111]([NH:110][C:113]4[CH:114]=[N:115][CH:116]=[CH:117][CH:118]=4)=[O:112])[CH2:66]3)[N:78]=[C:77]3[C:73]=2[N:74]=[CH:75][N:76]3[C@@H:79]2[CH2:83][C@H:82]([NH:84][C:85](=[O:88])[CH2:86][CH3:87])[C@@H:81]([OH:89])[C@H:80]2[OH:90])[CH:95]=[CH:96][CH:97]=[CH:98][CH:99]=1

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 27604933-IsocyanatopyridineHCID 59781437N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamideHCID 866226559-((1R,2S,3R,4S)-4-acetylamino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid {2-[3-(3,4,5,6-tetra-hydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethyl}-amide trifluoroacetate

Product 1

HCID 67019352N-((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Procedure

This compound is prepared analogously to 9-((1R,2S,3R,4S)-4-acetylamino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid {2-[3-(3,4,5,6-tetra-hydro-2H-[1,2′]bipyridinyl-4-yl)-ureido]-ethyl}-amide trifluoroacetate (Ex. 42) by replacing 9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid {2-[3-(3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-ureido]-ethyl}-amide dihydrochloride (an intermediate for preparing Example 38) with 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}-propionamide (Example 36) and by replacing acetyl chloride with 3-isocyanato-pyridine.

Sources & evidence

ORD record
ord-3a4ae4d968974bb9b26778c98d1c8347
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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