Trifluoroacetic acid → HCID 178484181, 화합물

HRID 1919170노트

반응식

HRID 1919170 반응식
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26].[NH:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]1[NH:38][C:39]([C:42]2[S:43][C:44]([C:47]3[S:51][C:50]([C:52]4[NH:56][C:55]([C@@H:57]5[CH2:61][CH2:60][CH2:59][NH:58]5)=[N:54][CH:53]=4)=[N:49][CH:48]=3)=[CH:45][N:46]=2)=[CH:40][N:41]=1.Cl.[CH3:63][N:64]([CH3:75])[C@H:65]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:66](O)=[O:67].C[CH2:77][N:78]([CH:82]([CH3:84])[CH3:83])[CH:79](C)C>CN(C)C=O.CO.O>[F:28][C:27]([F:30])([F:29])[C:25]([O-:31])=[O:26].[S:43]1[C:44]([C:47]2[S:51][C:50]([C:52]3[N:56]=[C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:83](=[O:26])[C@@H:82]([C:84]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:78]([CH3:77])[CH3:79])[NH:54][CH:53]=3)=[N:49][CH:48]=2)=[CH:45][N:46]=[C:42]1[C:39]1[N:38]=[C:37]([C@@H:33]2[CH2:34][CH2:35][CH2:36][N:32]2[C:66](=[O:67])[C@@H:65]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[N:64]([CH3:75])[CH3:63])[NH:41][CH:40]=1

참가 물질

10

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45835119(R)-a-(Dimethylamino)benzeneacetic acid HClHCID 53233526HCID 53233526, 화합물

생성물 2

HCID 84468TrifluoroacetateHCID 178484181HCID 178484181, 화합물수율 34%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

HATU (66 mg, 0.17 mmol) was added to a stirred solution of a TFA salt of 2,2′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-5-yl)-5,5′-bi-1,3-thiazole (40 mg, 0.045 mmol), (R)-2-(dimethylamino)-2-phenylacetic acid hydrochloride (39 mg, 0.18 mmol) and DIEA (0.078 mL, 0.45 mmol) in dimethylformamide (2 mL) at room temperature. The reaction was stirred for 3 h, diluted with methanol (2 mL) and water (2 mL) and stirred for 15 min. The reaction mixture was concentrated in vacuo to dryness and purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u, eluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA). Fractions containing the desired product were concentrated to yield a trifluoroacetate salt of (1R,1′R)-2,2′-(5,5′-Bi-1,3-thiazole-2,2′-diylbis(1H-imidazole-4,2-diyl(2S)-2,1-pyrrolidinediyl))bis(N,N-dimethyl-2-oxo-1-phenylethanamine) (18 mg, 0.015 mmol, 34% yield) as an orange solid.

후처리

  1. stirringstirred for 15 min
  2. concentrationThe reaction mixture was concentrated in vacuo to dryness
  3. custompurified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u
  4. washeluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA)
  5. additionFractions containing the desired product
  6. concentrationwere concentrated

출처 및 근거

ORD 기록
ord-0c5fe72377ee41a6a1b80e06c60bf77c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618153B2

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