Triethylamine → 6-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-methylphenyl)hexanamide

HRID 1926195ノート

反応式

HRID 1926195 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][C:23](O)=[O:24])=[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.[CH3:55][C:56]1[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([NH2:63])[CH:57]=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][C:23]([NH:62][C:59]3[CH:60]=[CH:61][C:56]([CH3:55])=[CH:57][C:58]=3[NH2:63])=[O:24])=[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

8

反応物 5

HCID 8471TriethylamineHCID 103323,4-DiaminotolueneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574954166-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 445403416-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-methylphenyl)hexanamide収率 84%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid (335 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), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 4-methyl-o-phenylenediamine (146 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 (369 mg, 84% yield) as a brown solid. 1H NMR (DMSO-d6) δ1.39 (m, 2H, CH2), 1.57 (m, 2H, CH2), 1.63 (m, 2H, CH2), 2.11 (s, 3H, CH3), 2.31 (t, J=8.0 Hz, 2H, CH2CO), 3.27 (m, 2H, NCH2), 4.72 (s, 2H, benzene-NH2), 6.31 (d, J=8.0 Hz, 1H, Ar—H), 6.61 (s, 1H, Ar—H), 6.99 (d, J=8.0 Hz, 1H, Ar—H), 7.08 (s, 1H, ═CH—CO), 7.33 (m, 2H, Ar—H), 7.40 (m, 2H, Ar—H), 7.76 (d, J=8.0 Hz, 1H, Ar—H), 7.82 (m, 2H, Ar—H), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.69 (d, J=8.0 Hz, 1H, Ar—H), 9.08 (s, 1H, benzene-NH). LC-MS (m/z) 440 (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-a3aa1803a68c452c88e05a805aabbab9
出典データセット
uspto-grants-2012_05
特許番号
US08178577B2

反応ノート

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