Formic Acid → N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-hydrazino-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 2382424Notes

Reaction equation

HRID 2382424 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]2[OH:22])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1.O.[NH2:39][NH2:40].C(O)(C)C.C(O)=O>C(#N)C>[C:26]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][NH:23][C:4]2[N:3]=[C:2]([NH:39][NH2:40])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]2[OH:22])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 3776IsopropanolHCID 24654Hydrazine hydrate (1:1)HCID 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide2×

Product 1

HCID 66630796N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-hydrazino-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Intermediate J) (1.0 g, 1.91 mmol) and hydrazine monohydrate (12 ml) is stirred for 72 h and then isopropyl alcohol (10 ml) is added. The solvent is removed in vacuo and the residue is water (10 ml) and stirred for 12 h. The fine solid obtained is filtered, washed with water and dried in vacuo to afford the product. LC-MS (0.1% formic acid, acetonitrile) (MH+ 517)

Workup

  1. customThe solvent is removed in vacuo
  2. customThe fine solid obtained
  3. filtrationis filtered
  4. washwashed with water
  5. customdried in vacuo
  6. customto afford the product

Sources & evidence

ORD record
ord-75abb8a99f0a4bb89a27ff7ad1942b86
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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