Oxalyl chloride → Tert-butyl 2-(5-bromobenzo[d]oxazole-2-carboxamido)-4-(4-chlorophenyl)thiophene-3-carboxylate

HRID 390776노트

반응식

HRID 390776 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[N:7][C:6]=2[CH:13]=1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[C:25]=1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:20][C:21]3[S:22][CH:23]=[C:24]([C:33]4[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=4)[C:25]=3[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:12])=[N:7][C:6]=2[CH:13]=1

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 513585535-Bromobenzo[d]oxazole-2-carboxylic acidHCID 59535972HCID 59535972, 화합물

생성물 1

HCID 67207536Tert-butyl 2-(5-bromobenzo[d]oxazole-2-carboxamido)-4-(4-chlorophenyl)thiophene-3-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 5-bromobenzo[d]oxazole-2-carboxylic acid (2A, 60 mg, 0.25 mmol) in DCM (5 ml) at room temperature was added oxalyl chloride (0.2 ml) and catalytic amount of DMF. The mixture was stirred at room temperature for 17 hours. The solvent was removed under vacuum to dryness. The residue was dissolved in DCM (5 ml) followed be addition of tert-butyl 2-amino-4-(4-chlorophenyl)thiophene-3-carboxylate (1A, 62 mg, 0.2 mmol) and DIEA (0.3 ml). The mixture was stirred at room temperature for 17 hours. The reaction mixture was diluted with DCM (5 ml) washed with 1N aqueous HCl (3×5 ml), water (1×5 ml), 1N aqueous NaOH (3×5 ml) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under vacuum to give analytically pure 3A which was used in the next step without further purification. LC-MS: calcd. for C23H18BrClN2O4S: 532 (M+1); found: 532.

후처리

  1. customThe solvent was removed under vacuum to dryness
  2. dissolutionThe residue was dissolved in DCM (5 ml)
  3. stirringThe mixture was stirred at room temperature for 17 hours
  4. washwashed with 1N aqueous HCl (3×5 ml), water (1×5 ml), 1N aqueous NaOH (3×5 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationThe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-3b0d2e21ad254800a2ec7a92d960af6e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383670B2

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