Acetone → 2-[5-Chloro-2-(12-isopropyl-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide

HRID 1040624노트

반응식

HRID 1040624 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]12[NH:26][CH:23]([CH2:24][CH2:25]1)[CH2:22][C:21]1[CH:20]=[CH:19][C:18]([NH:27][C:28]3[N:33]=[C:32]([NH:34][C:35]4[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=4[C:37]([NH:39][CH3:40])=[O:38])[C:31]([Cl:45])=[CH:30][N:29]=3)=[CH:17][C:16]2=1.[CH3:46][C:47]([CH3:49])=O.ClC(Cl)C>C(O)(=O)C>[Cl:45][C:31]1[C:32]([NH:34][C:35]2[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=2[C:37]([NH:39][CH3:40])=[O:38])=[N:33][C:28]([NH:27][C:18]2[CH:19]=[CH:20][C:21]3[CH2:22][CH:23]4[N:26]([CH:47]([CH3:49])[CH3:46])[CH:15]([CH2:25][CH2:24]4)[C:16]=3[CH:17]=2)=[N:29][CH:30]=1

참가 물질

6

반응물 4

HCID 180AcetoneHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 668293732-[2-(12-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzamide

생성물 1

HCID 668295692-[5-Chloro-2-(12-isopropyl-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide수율 82%

시약·촉매·용매 1

HCID 176Acetic Acid촉매

실험 절차

Sodium triacetoxyborohydride (100 mg, 0.47 mmol) was added to a solution of 2-[2-(12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzamide (100 mg, 0.23 mmol), acetone (0.034 mL, 0.47 mmol), acetic acid (1 drop) and dichloroethane (5 mL). The reaction was stirred at room temperature for 18 h. The reaction was then quenched with saturated aqueous NaHCO3 (5 mL), extracted with CH2Cl2 (2×5 mL), dried over MgSO4, filtered, and concentrated to afford the title compound as off-white solid (89 mg, 82%). 1HNMR (400 MHz, DMSO-d6) δ 11.6 (s, 1H), 9.3 (s, 1H), 8.8-8.7 (m, 2H), 8.2 (s, 1H), 7.8 (d, 1H, J=7.8 Hz), 7.5 (appt t, 1H, J=8.1 Hz), 7.4 (d, 1H, J=8.6), 7.3 (s, 1H), 7.1 (appt t, 1H, J=7.6 Hz), 6.9 (d, 1H, J=8.3 Hz), 3.9 (m, 1H), 3.6 (m, 1H), 3.0 (dd, 1H, J=17.2, 4.6 Hz), 2.8 (d, 3H, J=4.3 Hz), 2.4 (m, 1H), 2.2 (d, 1H, J=17.2 Hz), 2.1-2.0 (m, 2H), 1.6 (m, 1H), 1.5 (m, 1H), 1.1 (d, 3H, J=5.9 Hz), 0.9 (d, 3H, J=5.9 Hz); MS (m/e) 477 (M+1); mp 202-205° C.

후처리

  1. customThe reaction was then quenched with saturated aqueous NaHCO3 (5 mL)
  2. extractionextracted with CH2Cl2 (2×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1822634ff86e4b479d6c9305d02b677d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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