Sulfuric Acid → (2R,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one sulfuric acid salt

HRID 626917노트

반응식

HRID 626917 반응식
[CH3:1][N:2]1[CH2:27][CH2:26][C:4]2([NH:8][CH:7]([C:9]3[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)[N:10]=3)[CH2:6][CH2:5]2)[C:3]1=[O:28].[S:29](=[O:33])(=[O:32])([OH:31])[OH:30]>CC#N>[S:29](=[O:31])(=[O:30])([OH:33])[OH:32].[CH3:1][N:2]1[CH2:27][CH2:26][C@:4]2([NH:8][C@@H:7]([C:9]3[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([C:16]4[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=4)[N:10]=3)[CH2:6][CH2:5]2)[C:3]1=[O:28]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 725484337-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one

생성물 1

HCID 72548434(2R,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one sulfuric acid salt

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A similarly prepared sample was recrystallised from diethyl ether and isohexane to give the free base form of the title material as a colorless solid with a melting point of 66-67° C. Similarly prepared 7-methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one with a diastereomeric excess of approximately 92% (49 g, 125.51 mmol) in MeCN (700 mL) was suction filtered through a shallow pad of Hyflo to give a clear yellow solution. To this rapidly stirred solution at 50° C. was added 7.5M sulphuric acid (17.6 mL, 132 mmol) over 5 seconds to give a solution which quickly crystallized. The mixture was left to stand at ambient temperature for 2 h then filtered and washed with acetonitrile/Et2O (1:1) (200 ml) then Et2O (150 ml) and dried 50° C. to give the title material (E7a) in an 82:1 ratio of (2R,5S) and (2S,5S) isomers (50.6 g) assessed by NMR.

후처리

  1. customA similarly prepared sample was recrystallised from diethyl ether and isohexane
  2. customto give the free base form of the title material as a colorless solid with a melting point of 66-67° C
  3. filtrationfiltered through a shallow pad of Hyflo
  4. customto give a clear yellow solution
  5. customto give a solution which
  6. customquickly crystallized
  7. waitThe mixture was left
  8. filtrationthen filtered
  9. washwashed with acetonitrile/Et2O (1:1) (200 ml)
  10. dry with materialEt2O (150 ml) and dried 50° C.

출처 및 근거

ORD 기록
ord-46edb4018440476ba3b276f35d73657b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309254B2

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