N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide → Trifluoroacetic acid

HRID 2382448Notes

Reaction equation

HRID 2382448 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[CH:17][N:18]2[C@@H:21]2[CH2:25][C@H:24]([NH:26][C:27](=[O:30])[CH2:28][CH3:29])[C@@H:23]([OH:31])[C@H:22]2[OH:32])=[C:14]([NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:13]=1.[N:48]1([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=2)[CH2:53][CH2:52][CH:51]([NH:54][C:55](N2C=CN=C2)=[O:56])[CH2:50][CH2:49]1>CC(O)C.C(Cl)Cl>[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:42]1([CH:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:34][NH:33][C:14]2[N:13]=[C:12]([NH:11][CH2:10][CH2:9][NH:8][C:55]([NH:54][CH:51]3[CH2:50][CH2:49][N:48]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=4)[CH2:53][CH2:52]3)=[O:56])[N:20]=[C:19]3[C:15]=2[N:16]=[CH:17][N:18]3[C@@H:21]2[CH2:25][C@H:24]([NH:26][C:27](=[O:30])[CH2:28][CH3:29])[C@@H:23]([OH:31])[C@H:22]2[OH:32])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 2

HCID 21978278N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide2×HCID 66630999N-{(1S,2R,3S,4R)-4-[2-(2-Amino-ethylamino)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide trifluoroacetate

Product 2

HCID 6422Trifluoroacetic acidHCID 66630610N-[(1S,2R,3S,4R)-4-(6-(2,2-Diphenyl-ethylamino)-2-{2-[3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethylamino}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide trifluoroacetate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-{(1S,2R,3S,4R)-4-[2-(2-amino-ethylamino)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide trifluoroacetate (Example 100) (27 mg, 37 μmol) in IPA (0.5 ml) is treated with imidazole-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amide (Intermediate C) (1.1 ml of a 10 mg/ml solution in DCM, 40 μmol). After stirring at room temperature for 7 days, the solvent is removed in vacuo and purification of the residue by C-18 reverse phase column chromatography eluting with acetonitrile:water:TFA (0.1%) (gradient of 0 to 100% acetonitrile) yields the title compound. (MH+ 748.6)

Workup

  1. customthe solvent is removed in vacuo and purification of the residue by C-18 reverse phase column chromatography
  2. washeluting with acetonitrile

Sources & evidence

ORD record
ord-3e42bf6db44f4d1bae87fa45ac6d7fe9
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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