1,2-Dichloroethane → Hydrochloric Acid

HRID 1882578Notes

Reaction equation

HRID 1882578 reaction equation
[NH2:1][C@H:2]1[CH2:6][C@@H:5]([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH:36][C:37]([NH:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[O:38])[CH2:32]2)=[N:11][C:12]=3[NH:16][CH2:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:4]([OH:46])[C@@H:3]1[OH:47].[CH:48](=O)[CH2:49][CH3:50].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:66]CCCl>>[ClH:66].[ClH:66].[OH:46][C@@H:4]1[C@H:3]([OH:47])[C@@H:2]([NH:1][CH2:48][CH2:49][CH3:50])[CH2:6][C@H:5]1[N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][C:10]([N:31]1[CH2:35][CH2:34][C@@H:33]([NH:36][C:37]([NH:39][C:40]3[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=3)=[O:38])[CH2:32]1)=[N:11][C:12]=2[NH:16][CH2:17][CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 666296911-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea

Product 2

HCID 313Hydrochloric AcidHCID 666303611-{(r)-1-[9-((1r,2s,3r,4s)-2,3-Dihydroxy-4-propylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9h-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea hydrochloride

Procedure

A solution of 1-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea (Example 26 step 2) (17 mg, 26 mmol) in DCE (1 ml) is treated with propanaldehyde (1.5 mg, 26 mmol) and placed under an atmosphere of argon. Sodium triacetoxyborohydride (10 mg, 51 μmol) is added and the reaction mixture is stirred at room temperature overnight. The mixture is quenched with 2M NaOH (5 drops) and the solvent is removed in vacuo. The residue is purified by C-18 reverse phase column chromatography eluting with acetonitrile:water:HCl (0.1%) (gradient of 20 to 100% acetonitrile) to yield the title compound. (MH+ 677.14)

Workup

  1. customThe mixture is quenched with 2M NaOH (5 drops)
  2. customthe solvent is removed in vacuo
  3. customThe residue is purified by C-18 reverse phase column chromatography
  4. washeluting with acetonitrile

Sources & evidence

ORD record
ord-9b2f206f69644ca18fced250087d2bd5
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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