Sodium Hydroxide → Tert-butyl{2-[({5-[(chloroacetyl)amino]-benzothien-2-yl}carbonyl)amino]-phenyl}carbamate

HRID 1172869노트

반응식

HRID 1172869 반응식
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([C:14]([O:16]C)=O)=[CH:11][C:10]=2[CH:18]=1)=[O:4].[OH-:19].[Na+].ClCC(NC1C=C[C:29]2SC(C(O)=O)=[CH:31][C:30]=2[CH:37]=1)=O.CCN=C=NCCCN(C)C.[CH:49]1[CH:50]=[CH:51][C:52]2[N:57](O)N=[N:55][C:53]=2[CH:54]=1.C1[CH2:63][O:62]CC1.CO>CN(C=O)C.C(Cl)Cl>[C:30]([O:19][C:63](=[O:62])[NH:55][C:53]1[CH:54]=[CH:49][CH:50]=[CH:51][C:52]=1[NH:57][C:14]([C:12]1[S:13][C:9]2[CH:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][Cl:1])=[CH:18][C:10]=2[CH:11]=1)=[O:16])([CH3:29])([CH3:31])[CH3:37]

참가 물질

9

반응물 6

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21899815MeOH tetrahydrofuranHCID 252672155-(2-Chloroacetamido)benzo[b]thiophene-2-carboxylic acidHCID 57624569Methyl 5-[(chloroacetyl)amino]-1-benzothiophene-2-carboxylate

생성물 1

HCID 57624562Tert-butyl{2-[({5-[(chloroacetyl)amino]-benzothien-2-yl}carbonyl)amino]-phenyl}carbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 5-[(chloroacetyl)amino]-1-benzothiophene-2-carboxylate (1.26 g, 4.50 mmol) in THF/MeOH (16/16 μL) was added 2N NaOH (9 mL). After 4 h, the solvent was reduced and the aqueous was washed with EtOAc. The aqueous was acidified and the solids were filtered and used without further purification. To a solution of 5-[(chloroacetyl)amino]-1-benzothiophene-2-carboxylic acid (765 mg, 2.84 mmol) in DMF (3 mL) and CH2Cl2 (10 mL) was added EDCI (652 mg, 3.4 mmol), HOBt (460 mg, 3.40 mmol). The reaction mixture was stirred for 20 min and Boc-protected phenylene diamine (650 g, 3.12 mmol) was added. After 18 h, the solvent was removed and the residue was triturated with EtOAc and H2O. The solids were and filtered yielding the desired product as a solid, which was used without further purification. MS: cal'd 460 (MH+), exp 460 (MH+).

후처리

  1. washthe aqueous was washed with EtOAc
  2. filtrationthe solids were filtered
  3. customused without further purification
  4. additionBoc-protected phenylene diamine (650 g, 3.12 mmol) was added
  5. waitAfter 18 h
  6. customthe solvent was removed
  7. customthe residue was triturated with EtOAc and H2O
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-aa8ff8a5a80a48b882f53c28f00cd23b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834034B2

반응 노트

불러오는 중…