Hydrochloric Acid → N-(3-(4-(Ethylamino)cyclohexyl)-1H-indol-5-yl)thiophene-2-carboximidamide

HRID 2043526노트

반응식

HRID 2043526 반응식
[CH2:1]([N:3]([CH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])[CH:24]=3)[NH:19][CH:18]=2)[CH2:13][CH2:12]1)C(=O)OC(C)(C)C)[CH3:2].Cl>>[CH2:1]([NH:3][CH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])[CH:24]=3)[NH:19][CH:18]=2)[CH2:13][CH2:12]1)[CH3:2]

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 178465425HCID 178465425, 화합물

생성물 1

HCID 178463261N-(3-(4-(Ethylamino)cyclohexyl)-1H-indol-5-yl)thiophene-2-carboximidamide수율 112.7%

실험 절차

Compound 120 (0.26 g, 0.557 mmol) was treated with 1 N aqueous HCl solution at room temperature and the resulting solution was refluxed for 2 h. The reaction was brought to room temperature, filtered and washed with water (5 mL). The solvent was evaporated and crude was recrystallised from ethanol/ether to obtain compound 121 (0.23 g, 94%) as a solid in 2:3 ratio of diastereomers. 1H NMR (DMSO-d6) δ 1.22-1.29 (m, 3H), 1.53-1.62 (m, 2H), 1.80-2.16 (m, 6H), 2.74-3.23 (m, 4H), 7.08 (d, 1H, J=8.4 Hz), 7.24-7.52 (m, 3H), 7.68-7.72 (m, 1H), 8.14-8.18 (m, 2H), 8.59 (s, 1H), 8.97-9.09 (m, 2H), 9.64 (s, 1H), 11.20, 11.27 (2s, 1H), 11.42 (s, 1H); ESI-MS m/z (%): 367 (MH+ for free base, 18), 322 (100), 184 (19), 119 (39); ESI-HRMS calculated for C21H27N4S (MH+, free base), calculated: 367.1959; observed: 367.1950.

후처리

  1. temperaturethe resulting solution was refluxed for 2 h
  2. customwas brought to room temperature
  3. filtrationfiltered
  4. washwashed with water (5 mL)
  5. customThe solvent was evaporated
  6. customcrude was recrystallised from ethanol/ether

출처 및 근거

ORD 기록
ord-0e5034e7e9c3487182aa91eceadfcc54
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586620B2

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