Triethylamine → HCID 178492638, 화합물

HRID 1096883노트

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HRID 1096883 반응식
CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][CH3:32])[CH:30]=3)[C:25](O)=[O:26])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl.[NH:34]1[C:38]([C:39]2[CH:40]=[C:41]3[C:51](=[CH:52][CH:53]=2)[O:50][C:44]2([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:43][C:42]3=[O:54])=[N:37][N:36]=[N:35]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN1C(=O)CCC1.C(Cl)(Cl)Cl>[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([C:25]([N:47]4[CH2:48][CH2:49][C:44]5([CH2:43][C:42](=[O:54])[C:41]6[C:51](=[CH:52][CH:53]=[C:39]([C:38]7[NH:37][N:36]=[N:35][N:34]=7)[CH:40]=6)[O:50]5)[CH2:45][CH2:46]4)=[O:26])[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579309723-(1H-indol-5-yl)-5-methoxybenzoic acidHCID 178479612HCID 178479612, 화합물

생성물 1

HCID 178492638HCID 178492638, 화합물

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

WSC hydrochloride (52.5 mg, 0.274 mmol) was added to a mixture of 3-(1H-indol-5-yl)-5-methoxybenzoic acid (61.0 mg, 0.228 mmol), 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (73.4 mg, 0.228 mmol), HOBT (34.9 mg, 0.228 mmol), triethylamine (0.048 mL, 0.34 mmol), chloroform (0.4 mL) and NMP (0.8 mL), and stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile) to obtain the title compound as a pale yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ: 11.18 (1H, s), 8.43 (1H, d J=2.3 Hz), 8.25 (1H, dd, J=8.8, 2.3 Hz), 7.87-7.86 (1H, m), 7.47 (1H, d, J=8.4 Hz), 7.41 (1H, dd, J=8.4, 1.7 Hz), 7.39 (1H, t, J=2.8 Hz), 7.35 (1H, d, J=8.8 Hz), 7.26 (1H, dd, J=2.4, 1.5 Hz), 7.24 (1H, t, J=1.5 Hz), 6.87 (1H, dd, J=2.4, 1.5 Hz), 6.49 (1H, ddd, J=2.8, 2.1, 0.7 Hz), 4.37-4.23 (1H, m), 3.86 (3H, s), 3.66-3.18 (3H, m), 2.99 (2.0H, s), 2.14-1.81 (4H, m). MS [M−H]−=533.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile)

출처 및 근거

ORD 기록
ord-e64a538db44a4592ad23ae6921598aa2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138197B2

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