(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate → HCID 178448288, 화합물

HRID 245762노트

반응식

HRID 245762 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22].COC(=O)N[CH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([C:38]2[N:42]3[CH:43]=[CH:44][N:45]=[C:46]([CH3:47])[C:41]3=[C:40](Br)[N:39]=2)[CH2:34][CH2:33]1>>[CH3:21][O:20][C:19]([CH2:31][C@H:32]1[CH2:33][CH2:34][C@H:35]([C:38]2[N:42]3[CH:43]=[CH:44][N:45]=[C:46]([CH3:47])[C:41]3=[C:40]([C:7]3[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22])=[C:3]([O:2][CH3:1])[CH:8]=3)[N:39]=2)[CH2:36][CH2:37]1)=[O:26]

참가 물질

3

반응물 2

HCID 67364014(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamateHCID 178502113HCID 178502113, 화합물

생성물 1

HCID 178448288HCID 178448288, 화합물수율 117.1%

실험 절차

(S)-Pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (19 mg) and methyl((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (20 mg) were reacted according to the procedure described in example 4 step 4c and purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid). Proper fractions were collected and made basic with aqueous sodium hydrogencarbonate, extracted with dichloromethane, organic layer dried (Na2SO4) and concentrated in vacuo to give (S)-pentan-2-yl 4-(3-((trans)-4-(methoxycarbonylmethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate (16 mg).

후처리

  1. custompurified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid)
  2. customProper fractions were collected
  3. extractionextracted with dichloromethane, organic layer
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-54cff51c9f64422594586ebd17346b77
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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