Acetic Acid → 2-((3-(2-Oxa-6-azaspiro[3.5]nonan-6-ylmethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921819

반응식

HRID 921819 반응식
[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([C:10]#[N:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][CH:20]2[CH2:22][CH2:21]2)[C:16]2=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]2[N:14]=1.C(O)(=O)C.[CH2:32]1[C:35]2([CH2:40][CH2:39][CH2:38][NH:37][CH2:36]2)[CH2:34][O:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.ClCCCl>[CH2:32]1[C:35]2([CH2:40][CH2:39][CH2:38][N:37]([CH2:8][C:7]3[C:2]([Cl:1])=[C:3]([NH:12][C:13]4[N:18]=[C:17]([NH:19][CH:20]5[CH2:21][CH2:22]5)[C:16]5=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]5[N:14]=4)[CH:4]=[C:5]([C:10]#[N:11])[CH:6]=3)[CH2:36]2)[CH2:34][O:33]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 513419452-Oxa-6-azaspiro[3.5]nonaneHCID 867086482-((2-Chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

생성물 1

HCID 899340582-((3-(2-Oxa-6-azaspiro[3.5]nonan-6-ylmethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of 2-((2-chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 400) (20 mg, 0.053 mmol), acetic acid (9.07 tli, 0.158 mmol) and 2-oxa-6-azaspiro[3.5]nonane (16.79 mg, 0.132 mmol) in THF (0.5 ml) was stirred at room temperature to for 5 min. to achieve solution. DCE (0.5 mL) was added and after 25 min, sodium triacetoxyborohydride (33.6 mg, 0.158 mmol) was added. LCMS analysis found the desired mass of the product. The mixture was stirred overnight. The reaction mixture was then quenched with saturated aqueous NaHCO3 and stirred for 10 minutes. It was dried with a stream of nitrogen and then dissolved in DMF (1.5 mL) and purified by reverse-phase preparative LCMS.

후처리

  1. stirringThe mixture was stirred overnight
  2. customThe reaction mixture was then quenched with saturated aqueous NaHCO3
  3. stirringstirred for 10 minutes
  4. customIt was dried with a stream of nitrogen
  5. dissolutiondissolved in DMF (1.5 mL)
  6. custompurified by reverse-phase preparative LCMS

출처 및 근거

ORD 기록
ord-9ff3a299ca2b43ebaac89b4420243370
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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