Triethylamine → Methyl 4-[(2-amino-5-iodo-benzoylamino)-methyl]-benzoate

HRID 1062585

반응식

HRID 1062585 반응식
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.[NH2:32][C:33]1[CH:41]=[CH:40][C:39]([I:42])=[CH:38][C:34]=1[C:35](O)=[O:36].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:32][C:33]1[CH:41]=[CH:40][C:39]([I:42])=[CH:38][C:34]=1[C:35]([NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1)=[O:36]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 22281877Methyl 4-[(2-amino-5-iodo-benzoylamino)-methyl]-benzoate수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 15 g (74.4 mmol) of methyl 4-(aminomethyl)benzoate hydrochloride, 300 ml of dimethylformamide and 10.3 ml (7.53 g, 74.4 mmol) of triethylamine were added, at room temperature, followed by 10.06 g (74.4 mmol) of 1-hydroxybenzotriazole hydrate, 19.6 g (74.4 mmol) of 2-amino-5-iodobenzoic acid and 14.3 g (74.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. After stirring at room temperature overnight, the mixture was concentrated and the residue was dissolved in 300 ml of dichloromethane. The organic phase was washed with 150 ml H2O, 150 ml HCl 1N, and 150 ml H2O, dried over sodium sulfate and concentrated. The residue was recrystallized from 170 ml acetonitrile to afford after filtration 19.6 g of the desired product (yield: 70%).

후처리

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in 300 ml of dichloromethane
  3. washThe organic phase was washed with 150 ml H2O, 150 ml HCl 1N, and 150 ml H2O
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from 170 ml acetonitrile
  7. customto afford

출처 및 근거

ORD 기록
ord-fc77ddb5ab5549c5b7e3d30e19bd348e
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962922B2

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