Triethylamine → {4-[4-(1-Ethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-methanol hydrochloride

HRID 220572

反応式

HRID 220572 の反応式
[ClH:1].Cl.[N:3]1([C:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=3)=[N:13][CH:12]=[CH:11][N:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH2:23]([N:25]1[CH:29]=[C:28]([CH:30]=O)[CH:27]=[N:26]1)[CH3:24].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClC(Cl)C.C(=O)(O)[O-].[Na+].CO.C(O)(=O)C>[ClH:1].[CH2:23]([N:25]1[CH:29]=[C:28]([CH2:30][N:6]2[CH2:7][CH2:8][N:3]([C:9]3[C:14]([C:15]4[CH:16]=[CH:17][C:18]([CH2:21][OH:22])=[CH:19][CH:20]=4)=[N:13][CH:12]=[CH:11][N:10]=3)[CH2:4][CH2:5]2)[CH:27]=[N:26]1)[CH3:24]

参加物

10

反応物 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27589001-Ethyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68595263[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol dihydrochloride

生成物 1

HCID 68595506{4-[4-(1-Ethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-methanol hydrochloride収率 83.1%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Combine [4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-methanol dihydrochloride (0.177 g, 0.516 mmol), 1-ethyl-1H-pyrazole-4-carbaldehyde (0.064 g, 0.516 mmol) and triethylamine (0.144 mL, 1.03 mmol) in dichloroethane (4 mL). Add glacial acetic acid (42 mL) followed by sodium triacetoxyborohydride (0.153 g, 0.722 mmol). Stir at room temperature for 20 hr. Dilute with saturated aq. sodium bicarbonate then extract three times using DCM. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM), to give a white solid. Dissolve the solid in methanol and add ammonium chloride (1 equivalent) then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a white solid (0.178 g, 83%). MS (ES): m/z=379

後処理

  1. extractionthen extract three times
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM)
  7. customto give a white solid
  8. customthen sonicate the mixture for 10 min
  9. customEvaporate the solution

出典と根拠

ORDレコード
ord-01fb991012494ad28fc6df9defbb02b9
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

関連ノート

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