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Trifluoroacetic acid → 4-[3-((R)-3-Amino-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-[1,4]oxazepin-5-yl)-4-fluoro-phenylamino]-benzonitrile

HRID 403274
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HRID 403274 반응식
COC1C=CC(C(C2C=CC(OC)=CC=2)([NH:16][C:17]2[CH2:18][O:19][CH2:20][C:21]([F:42])([F:41])[C@:22]([C:25]3[CH:26]=[C:27]([NH:32][C:33]4[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=4)[CH:28]=[CH:29][C:30]=3[F:31])([CH3:24])[N:23]=2)C2C=CC=CC=2)=CC=1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[NH2:16][C:17]1[CH2:18][O:19][CH2:20][C:21]([F:41])([F:42])[C@:22]([C:25]2[CH:26]=[C:27]([NH:32][C:33]3[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=3)[CH:28]=[CH:29][C:30]=2[F:31])([CH3:24])[N:23]=1
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참가 물질

5

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HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 68227192(R)-4-(3-(3-(bis(4-methoxyphenyl)(phenyl)methylamino)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-5-yl)-4-fluorophenylamino)benzonitrile

생성물 1

HCID 665473204-[3-((R)-3-Amino-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-[1,4]oxazepin-5-yl)-4-fluoro-phenylamino]-benzonitrile수율 76.7%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
23 °C

실험 절차

To a solution of (R)-4-(3-(3-(bis(4-methoxyphenyl)(phenyl)methylamino)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-5-yl)-4-fluorophenylamino)benzonitrile (intermediate A13A) (21 mg, 31 μmol) in dichloromethane (1 ml) at 23° C. was added trifluoroacetic acid (370 mg, 250 μl, 3.24 mmol) and the mixture was stirred at 23° C. for 1 h. Poured into sat. Na2CO3-sol., extracted thrice with ethyl acetate, dried the combined organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product, which was purified by preparative HPLC (column: Gemini 5μ C18 110 A° AXIA (50×21.2 mm); flow: 40 ml/min; gradient: water (+0.1% TEA)/acetonitrile (90%-10% 1 min plateau; in 3.5 min to 5%-95%); collection: UV-detector 300 nm) to give the title compound (8.9 mg, 76.6%) after trituration with little diethyl ether/pentane as a white solid. MS (ISP): m/z=375.3 [M+H]+.

후처리

  1. extraction, extracted thrice with ethyl acetate
  2. dry with materialdried the combined organic layer over Na2SO4
  3. customRemoval of the solvent in vacuum
  4. waitleft a crude product, which
  5. customwas purified by preparative HPLC (column: Gemini 5μ C18 110 A° AXIA (50×21.2 mm); flow: 40 ml/min; gradient: water (+0.1% TEA)/acetonitrile (90%-10% 1 min plateau; in 3.5 min to 5%-95%); collection: UV-detector 300 nm)

출처 및 근거

ORD 기록
ord-d0ca0c26c12c4c0cbfd61d4731c4f001
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748418B2

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