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Triethylamine → 8-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-fluorophenyl)octanamide

HRID 1926207
ノート
印刷プレビュー

反応式

HRID 1926207 の反応式
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[F:57][C:58]1[CH:63]=[CH:62][C:61]([NH2:64])=[C:60]([NH2:65])[CH:59]=1>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:64][C:61]3[CH:62]=[CH:63][C:58]([F:57])=[CH:59][C:60]=3[NH2:65])=[O:26])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8471TriethylamineHCID 1645844-Fluorobenzene-1,2-diamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579720638-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 44540437
8-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-fluorophenyl)octanamide
収率 70%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid (363 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxyl-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 4-fluoro-o-phenylenediamine (151 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (330 mg, 70% yield) as a brown solid. 1H NMR (DMSO-d6) δ1.33 (m, 6H, 3×CH2), 1.52 (m, 2H, CH2), 1.58 (m, 2H, CH2), 2.29 (t, J=8.0 Hz, 2H, CH2CO), 3.24 (m, 2H, NCH2), 5.12 (s, 2H, benzene-NH2), 6.28 (t, J=8.0 Hz, 1H, Ar—H), 6.46 (d, J=8.0 Hz, 1H, Ar—H), 7.08 (s, 1H, ═CH—CO and Ar—H), 7.33 (m, 2H, Ar—H), 7.41 (m, 2H, Ar—H), 7.76 (d, J=8.0 Hz, 1H, Ar—H), 7.82 (m, 2H, Ar—H), 8.52 (t, J=4.0 Hz, 1H, CONH), 8.67 (d, J=8.0 Hz, 1H, Ar—H), 9.02 (s, 1H, benzene-NH). LC-MS (m/z) 472 (M+1).

後処理

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-30c93781f84344c2b2eacd986bddf842
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178577B2

反応ノート

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