1,2-Dichloroethane → Hydrochloric Acid

HRID 1882578노트

반응식

HRID 1882578 반응식
[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

참가 물질

6

반응물 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

생성물 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

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-9b2f206f69644ca18fced250087d2bd5
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318750B2

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