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

HRID 1926207
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HRID 1926207 반응식
[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
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참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-30c93781f84344c2b2eacd986bddf842
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178577B2

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