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 1751101ノート

反応式

HRID 1751101 の反応式
[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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-5e750f7cb16c47a6ba1027c515680b8b
出典データセット
uspto-grants-2015_10
特許番号
US09156840B2

反応ノート

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