Hydrochloric Acid → HCID 71575882、化合物

HRID 1037008ノート

反応式

HRID 1037008 の反応式
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]

参加物

6

反応物 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、化合物HCID 866854534-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

生成物 1

HCID 71575882HCID 71575882、化合物収率 54%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-cab64c0ead4e41cda59b9101397891bd
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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