Triphenylphosphine → 4-[1-(2-Dimethylamino-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 719505

반응식

HRID 719505 반응식
[CH3:1][N:2]([CH3:23])[C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([OH:22])=[C:16]2[CH:15]=[N:14]1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34](O)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([O:22][C:21]2[N:20]=[CH:19][N:18]=[C:17]3[N:13]([C:4]4[CH:5]=[CH:6][C:7]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:8][C:3]=4[N:2]([CH3:23])[CH3:1])[N:14]=[CH:15][C:16]=23)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178482971HCID 178482971, 화합물

생성물 1

HCID 536304064-[1-(2-Dimethylamino-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

1-(2-Dimethylamino-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (66 mg, 0.200 mmol), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (61 mg, 0.300 mmol) and triphenylphosphine (52 mg, 0.200 mmol) were dissolved in toluene (5 mL) and the mixture stirred at 0° C. for 15 min. Diisopropyl azodicarboxylate (28 μL, 0.200 mmol) was then added and the reaction kept going at rt for 16 h. The solvent was removed under reduced pressure and the crude was purified by HPLC. Compound A100 was obtained as a yellowish solid. Exact mass calculated for C24H32N6O5S 516.22, found 517.3 (MH+, 100%). 1H NMR (400 MHz CDCl3) δ (ppm): 8.50 (s, 1H); 8.22 (s, 1H); 7.42(m, 3H); 5.52 (m, 1H); 3.81 (m, 2H); 3.26 (m, 2H); 3.03 (s, 3H); 2.47 (s, 6H); 2.03 (m, 2H); 1.80 (m, 2H); 1.42 (s, 9H).

후처리

  1. waitthe reaction kept going at rt for 16 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude was purified by HPLC
  4. customwas obtained as a yellowish solid

출처 및 근거

ORD 기록
ord-b084e0eb2bc0459dad6cef1bd765552c
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132426B2

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