Diisopropylethylamine → 4-Chloro-1-{[5-(1,3-dimethyl-1H-pyrazol-5-yl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-1H-indole-5-carbonitrile

HRID 913624

반응식

HRID 913624 반응식
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:19][CH2:20][CH3:21])[N:6]2[CH2:13]/[C:14](=[N:17]/[H])/[NH:15][OH:16].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[CH3:40][N:41]1[C:45]([C:46](O)=O)=[CH:44][C:43]([CH3:49])=[N:42]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:19][CH2:20][CH3:21])[N:6]2[CH2:13][C:14]1[N:17]=[C:46]([C:45]2[N:41]([CH3:40])[N:42]=[C:43]([CH3:49])[CH:44]=2)[O:16][N:15]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 5877211,3-Dimethyl-1H-pyrazole-5-carboxylic acidHCID 178506478HCID 178506478, 화합물

생성물 1

HCID 578003364-Chloro-1-{[5-(1,3-dimethyl-1H-pyrazol-5-yl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-1H-indole-5-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Synthesized as described in Example 32A and Example 33 using (1Z)-2-(4-chloro-5-cyano-2-propyl-1H-indol-1-yl)-N-hydroxyethanimidamide (0.030 g, 0.1 mmol) in anhydrous THF (5 mL) with propanephosphonic acid cyclic anhydride (T3P) (0.034 g, 0.12 mmol), 1,3-dimethyl-1H-pyrazole-5-carboxylic acid (0.014 g, 0.1 mmol) and DIEA (0.016 g, 0.12 mmol) and stirred at rt for 1 h and then heated at 120° C. for 2 h in the microwave: 1H NMR (400 MHz, CDCl3) δ 7.90 (s, 1 H), 7.52 (d, J=8.6 Hz, 1 H), 7.46 (d, J=8.5 Hz, 1 H), 6.71 (s, 1 H), 5.44 (s, 2 H), 4.12 (s, 3 H), 2.97 (t, 2 H), 2.30 (s, 3 H), 1.80-1.72 (m, 2 H), 1.04 (t, 3 H); MS (ES) m/z 395 (M+1).

후처리

  1. customSynthesized
  2. temperatureheated at 120° C. for 2 h in the microwave

출처 및 근거

ORD 기록
ord-b02fda37f15d46c7a027f94e97c20291
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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