Triphenylphosphine → 5-tert-Butyl-2-{4-chloro-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-2H-pyrazol-3-ylamine

HRID 60641

반응식

HRID 60641 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([Cl:14])=[C:11]([OH:13])[CH:12]=2)[N:5]=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][CH2:26][CH2:27]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[C:15]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:8]=[CH:9][C:10]([Cl:14])=[C:11]([O:13][CH2:27][CH2:26][O:25][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][O:19]3)[CH:12]=2)[N:5]=1)([CH3:18])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 5462977Diethyl azodicarboxylateHCID 689526455-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)-2-chlorophenol

생성물 1

HCID 1177296295-tert-Butyl-2-{4-chloro-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-2H-pyrazol-3-ylamine수율 89%

시약·촉매·용매 2

HCID 962Water촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-(5-Amino-3-tert-butyl-pyrazol-1-yl)-2-chloro-phenol (WO2011/154734A1, which is incorporated herein by reference, 340 mg, 1.28 mmol), 2-(tetrahydro-pyran-2-yloxy)-ethanol (0.26 mL, 1.92 mmol) and Ph3P (671 mg, 2.56 mmol) in dry THF (10 mL) was added diethylazodicarboxylate (0.41 mL, 2.56 mmol) and the mixture stirred for 10 min. Water (4 drops) was added and the mixture concentrated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (450 mg, 89%). LCMS (Method 3): Rt 3.73 min, m/z 394 [MH+].

후처리

  1. concentrationthe mixture concentrated in vacuo
  2. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-ca44b3f2f7e44f3a997e860badf044e0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440974B2

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