Formic Acid → 2-((1-(4-Fluorophenyl)-4-oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 2363032노트

반응식

HRID 2363032 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]5([CH2:31][CH2:30]5)[C:22]4=[O:32])[CH2:14][CH2:13]3)[C:11](=[O:33])[N:10]([CH2:34][C:35]3[CH:47]=[CH:46][CH:45]=[CH:44][C:36]=3[C:37]([O:39]C(C)(C)C)=[O:38])[CH2:9]2)=[CH:4][CH:3]=1.C(O)=O.C([SiH](CC)CC)C.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH2:20][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]5([CH2:30][CH2:31]5)[C:22]4=[O:32])[CH2:16][CH2:17]3)[C:11](=[O:33])[N:10]([CH2:34][C:35]3[CH:47]=[CH:46][CH:45]=[CH:44][C:36]=3[C:37]([OH:39])=[O:38])[CH2:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 58046675Tert-butyl 2-((1-(4-fluorophenyl)-4-oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

생성물 1

HCID 547722142-((1-(4-Fluorophenyl)-4-oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To tert-butyl 2-((1-(4-fluorophenyl)-4-oxo-8-(3-(2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.12 g, 0.19 mmol) was added concentrated formic acid (2 mL) and triethylsilane (0.05 mL). After stirring at room temperature for 18 hours, the reaction mixture was concentrated, isolated by pTLC (10% methanol/dichloromethane) and lyophilized with 4M HCl in dioxane (0.5 mL) to obtain the title compound as a hydrochloride salt (0.038 g, 33%); 1H NMR (DMSO-d6): δ 1.53 (t, 2H, J=3.6 Hz), 1.61 (t, 2H, J=3.6 Hz), 2.00 (d, 2H, J=14.4 Hz), 2.08 (t, 2H, J=8 Hz), 2.70 (t, 2H, J=13.6 Hz), 3.20 (br, 2H), 3.45-3.72 (m, 4H), 3.83 (t, 2H, J=7.2 Hz), 4.64 (s, 2H), 4.91 (s, 2H), 6.99-7.10 (m, 6H), 7.20-7.28 (m, 2H), 7.31 (d, 1H, J=7.6 Hz), 7.42 (t, 1H, J=7.6 Hz), 7.59 (t, 1H, J=6.8 Hz), 7.91 (dd, 1H, J=7.6 and 1.2 Hz), 10.26 (br, 1H), 13.18 (s, 1H); MS for C34H35FN4O4 m/z 583.3 (M+H)+.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. customisolated by pTLC (10% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-4a711d11478643eab2b2c8ac78d0464b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691836B2

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