Diisopropylethylamine → HCID 18617839, 화합물

HRID 1264239노트

반응식

HRID 1264239 반응식
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[C:29]#[N:30].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=O.O.C(O)(C(F)(F)F)=O.C(#N)C>CN(C=O)C>[C:29]([C:23]1[C:22]2[C:26](=[CH:27][CH:28]=[C:20]([CH2:19][CH2:18][NH:17][C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([CH:5]4[CH2:4][CH2:3][C:2](=[O:1])[NH:7][CH2:6]4)=[CH:16][CH:15]=3)[CH:21]=2)[NH:25][CH:24]=1)#[N:30]

참가 물질

8

반응물 6

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11217658HCID 11217658, 화합물HCID 18617602HCID 18617602, 화합물HCID 21924481TFA acetonitrileHCID 22392675Trifluoroacetic acid water

생성물 1

HCID 18617839HCID 18617839, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(6-Oxo-piperidin-3-yl)-benzoic acid (190 mg, 0.87 mmol, reference example 65) and 5-(2-amino-ethyl)-1H-indole-3-carbonitrile (161 mg, 0.87 mmol, reference example 2) is dissolved in anhydrous DMF (3 mL). To this solution is added diisoproplyethylamine (330 μl, 1.9 mmol), followed by HBTU (330 mg, 0.87 mmol) and allowed to stir at room temperature overnight (16 hours). The product is isolated by Reverse-Phase chromatography of the crude reaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes, A: 0.1% TFA/water, B: 0.1% TFA/acetonitrile). 1H NMR (300 MHz, DMSO) δ 1.94 (m, 2H), 2.26 (m, 2H), 2.92 (t, J=7.1, 2H), 3.19 (m, 1H), 3.48 (m, 2H), 3.46 (m, 2H), 7.13 (d, J=8.4, 1H), 7.15 (d, J=1.4, 2H), 7.36 (d, J=8.3, 2H), 7.43 (d, J=8.5, 1H), 7.46 (s, 1H), 7.55 (d, J=2.5, 1H), 7.73 (d, J=8.3, 2H), 8.17 (d, J=3.0, 1H), 8.47 (t, J=5.5, 1H). MS (Ion spray) m/z 387 (M+H)+.

후처리

  1. customThe product is isolated by Reverse-Phase chromatography of the crude
  2. customreaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes

출처 및 근거

ORD 기록
ord-4fcf2a382dfd4ceeba68e80d9cb7c222
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541505B1

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