Ammonium Chloride → 2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid

HRID 712154노트

반응식

HRID 712154 반응식
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[B:30]1(B2OCC(C)(C)CO2)[O:35]CC(C)(C)C[O:31]1.C([O-])(=O)C.[K+].[NH4+].[Cl-]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([B:30]([OH:35])[OH:31])=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 72724619HCID 72724619, 화합물

생성물 1

HCID 727244832-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid수율 88.6%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

To a stirred solution of [2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]trifluoromethanesulfonate (25 g, 56.1 mmol) in DMSO (250 mL) at rt was added bis(neopentylglycolato) diboron (25.20 g, 112.10 mmol) and potassium acetate (16.5 g, 168.2 mmol). The resulting reaction mixture was de-gassed by purging N2 for 15-20 min followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) DCM adduct (6.8 g, 8.4 mmol). The reaction mixture was again purged with N2for 15-20 min then heated to 80° C. for 90 min. After the completion of reaction (by TLC), the reaction mixture was poured onto saturated NH4Cl solution (1 L). The resulting precipitate was filtered and dried under vacuum. The solid cake was taken up in 2N NaOH (200 mL) and stirred for 45 min at rt. The solution was filtered and the filtrate acidified up to pH 5-6. The solid thus obtained was filtered and dried to obtain the desired product (17 g, 88%). 1H-NMR (DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 3.20 (m, 2H), 6.84 (br s, 1H), 7.41 (m, 1H), 8.01 (m, 1H), 8.12 (s, 1H), 8.25 (m, 3H), 8.40 (s, 1H), 8.79 (d, J=4.0 Hz, 1H) and 10.57 (br s, 1H). MS: 343.25 [M+H]+.

후처리

  1. customThe resulting reaction mixture
  2. customwas de-gassed
  3. customby purging N2 for 15-20 min
  4. customThe reaction mixture was again purged with N2for 15-20 min
  5. customAfter the completion of reaction (by TLC)
  6. filtrationThe resulting precipitate was filtered
  7. customdried under vacuum
  8. filtrationThe solution was filtered
  9. customThe solid thus obtained
  10. filtrationwas filtered
  11. customdried

출처 및 근거

ORD 기록
ord-fca422f74af14241b571973746bc3321
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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