Hydrochloric Acid → HCID 71575882, 화합물

HRID 1037008노트

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HRID 1037008 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[C:28]([C:34]2([C:49]([F:52])([F:51])[F:50])[O:38][N:37]=[C:36]([C:39]3[CH:47]=[CH:46][C:42]([C:43]([OH:45])=O)=[C:41]([CH3:48])[CH:40]=3)[CH2:35]2)[CH:29]=[C:30]([Cl:33])[C:31]=1[F:32].Cl.[NH2:54][CH2:55][C:56]1[CH:67]=[CH:66][C:59]2[B:60]([OH:65])[O:61][C:62]([CH3:64])([CH3:63])[C:58]=2[CH:57]=1.Cl>CC#N>[Cl:25][C:26]1[CH:27]=[C:28]([C:34]2([C:49]([F:51])([F:52])[F:50])[O:38][N:37]=[C:36]([C:39]3[CH:47]=[CH:46][C:42]([C:43]([NH:54][CH2:55][C:56]4[CH:67]=[CH:66][C:59]5[B:60]([OH:65])[O:61][C:62]([CH3:64])([CH3:63])[C:58]=5[CH:57]=4)=[O:45])=[C:41]([CH3:48])[CH:40]=3)[CH2:35]2)[CH:29]=[C:30]([Cl:33])[C:31]=1[F:32]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86685451HCID 86685451, 화합물HCID 866854534-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

생성물 1

HCID 71575882HCID 71575882, 화합물수율 54%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

HATU (350 mg, 0.92 mmol) was added to CH3CN (5 mL) at 0° C. After stirring for 5 min, the mixture was added to a solution of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (200 mg, 0.46 mmol), 5-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (157 mg, 0.69 mmol), and TEA (186 mg, 1.83 mmol) in CH3CN (8 mL). Then the solution was stirred at rt for 2 h. The solution was acidified with HCl (1 N) and extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by prep-TLC (PE:EA=2:1) to give the final title compound (150 mg, yield 54%). 1H NMR (300 MHz, DMSO-d6): δ 8.98 (s, 1H), 8.92 (t, J=6.0 Hz, 1H), 7.78 (d, 2H), 7.62-7.58 (m, 3H), 7.48-7.45 (m, 1H), 7.33-7.27 (m, 2H), 4.49 (d, 2H), 4.39-4.25 (m, 2H), 2.36 (s, 3H), 1.42 (s, 6H); HPLC purity: 97.6% at 254 nm; MS: m/z=609 [M+H]+.

후처리

  1. stirringThen the solution was stirred at rt for 2 h
  2. extractionextracted with EA
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by prep-TLC (PE:EA=2:1)

출처 및 근거

ORD 기록
ord-cab64c0ead4e41cda59b9101397891bd
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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