Acetic Acid → (2R,3R,4S,5R)-2-[6-[(2,2-Diphenylethyl)amino]-2-({[1-(2-pyridinyl)-4-piperidinyl]amino}methyl)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268385Notes

Reaction equation

HRID 2268385 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[N:61]1[CH2:66][CH2:65][C:64](=O)[CH2:63][CH2:62]1>>[C:25]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23][NH:22][C:5]2[N:4]=[C:3]([CH2:2][NH:1][CH:64]3[CH2:63][CH2:62][N:61]([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][N:55]=4)[CH2:66][CH2:65]3)[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolHCID 183483911-(Pyridin-2-yl)piperidin-4-one

Product 1

HCID 59975323(2R,3R,4S,5R)-2-[6-[(2,2-Diphenylethyl)amino]-2-({[1-(2-pyridinyl)-4-piperidinyl]amino}methyl)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 51%

Procedure

The title compound was prepared by a similar method to example 6 using (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (300 mg, 0.6 mmol), acetic acid (45 mg, 0.72 mmol), sodium triacetoxyborohydride (200 mg, 0.91 mmol) and 1-(2-pyridinyl)-4-piperidinone (120 mg, 0.66 mmol) (preparation 37). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (96:4:0.2) increasing in polarity to (93:7:0.3) to give the title compound (199 mg) as a foam. MS: 653 (MH+).

Workup

  1. customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (96:4:0.2)
  2. temperatureincreasing in polarity to (93:7:0.3)

Sources & evidence

ORD record
ord-1286546594144013afc2a0229104b03c
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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