Diisopropylethylamine → HCID 89907516, 화합물

HRID 629064노트

반응식

HRID 629064 반응식
CCN(C(C)C)C(C)C.[I:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([OH:16])=O.CN(C(ON1N=NC2C=CC(Cl)=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:46][C:47]([F:57])([F:56])[O:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1>C1COCC1.CN1C(=O)CCC1>[I:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([NH:53][C:52]1[CH:54]=[CH:55][C:49]([O:48][C:47]([F:46])([F:56])[F:57])=[CH:50][CH:51]=1)=[O:16]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6008484-(Trifluoromethoxy)anilineHCID 6216403-Iodo-4-methylbenzoic acidHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

생성물 1

HCID 89907516HCID 89907516, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

DIPEA (4.00 mL, 22.90 mmol) was added to a solution of 3-iodo-4-methylbenzoic acid (2 g, 7.63 mmol) and 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU, 3.47 g, 8.40 mmol) in THF (18 mL) and NMP (2 mL) and the RM was stirred at RT for 30 min. 4-(Trifluoromethoxy)aniline (1.536 mL, 11.45 mmol) was then added and the RM was stirred at RT for 14 h. The solvent was evaporated off under reduced pressure and the residue was treated with aq. 1M HCl (50 mL) and extracted with TBME. The combined extracts were washed with aq. 1 M HCl (50 mL), aq. sat. Na2CO3, water, brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure to give a residue which was crystallized from n-heptane/EtOAc to afford the title compound as white needles. UPLC-MS (Condition 1) tR=3.42 min, m/z=421.9-422.9 [M+H]+, m/z=419.9-420.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.44 (s, 3H) 7.36 (d, J=8.3 Hz, 2H) 7.49 (d, J=8.3 Hz, 1H) 7.83-7.93 (m, 3H) 8.39 (d, J=2.0 Hz, 1H) 10.42 (s, 1H).

후처리

  1. stirringthe RM was stirred at RT for 14 h
  2. customThe solvent was evaporated off under reduced pressure
  3. additionthe residue was treated with aq. 1M HCl (50 mL)
  4. extractionextracted with TBME
  5. washThe combined extracts were washed with aq. 1 M HCl (50 mL), aq. sat. Na2CO3, water, brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customto give a residue which
  9. customwas crystallized from n-heptane/EtOAc

출처 및 근거

ORD 기록
ord-1cf9a4f3bcc141c282d4bc492cbf687a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315489B2

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