Diisopropylethylamine → HCID 178468169, 화합물

HRID 2060059노트

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HRID 2060059 반응식
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](=[O:11])[N:8]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:7]=2[CH:18]=1.[CH2:19]([O:21][CH:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)[CH3:20].CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.CO>[CH2:19]([O:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([N:15]2[CH2:14][CH2:13][CH:12]([N:8]3[C:7]4[CH:18]=[C:3]([F:2])[CH:4]=[CH:5][C:6]=4[O:10][C:9]3=[O:11])[CH2:17][CH2:16]2)[CH2:24][CH2:23]1)[CH3:20]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 5464704-Ethoxycyclohexan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68479981HCID 68479981, 화합물

생성물 1

HCID 178468169HCID 178468169, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of 5-fluoro-3-(4-piperidinyl)-1,3-benzoxazol-2(3H)-one hydrochloride D138 (0.2 g), 4-(ethyloxy)cyclohexanone (WO2007107566) (0.2 g), and Hunig's base (0.1 g) in N-methylpyrrolidone (5 mL) was stirred for 2 hours then treated with sodium triacetoxyborohydride (0.5 g) was added and stirring was continued for four days. The mixture was diluted with methanol, loaded onto a SCX column and the column was eluted with methanol followed by 2M ammonia in methanol. The methanolic ammonia fractions were evaporated and the residue was purified by high pH MDAP. Two peaks were collected and evaporated separately. The fast eluting isomer gave 3-{1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinyl}-5-fluoro-1,3-benzoxazol-2(3H)-one E52 as a white solid (7 mg).

후처리

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for four days
  4. washthe column was eluted with methanol
  5. customThe methanolic ammonia fractions were evaporated
  6. customthe residue was purified by high pH MDAP
  7. customTwo peaks were collected
  8. customevaporated separately

출처 및 근거

ORD 기록
ord-243fe2e4b9244f8ba5a032a372d51445
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278328B2

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