Acetic Acid → 1-Methylethyl {(cis)-1-acetyl-2-methyl-6-[2-(1-piperidinylmethyl)-1,3-thiazol-4-yl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

HRID 2366921노트

반응식

HRID 2366921 반응식
[CH3:1][CH:2]([O:4][C:5](=[O:28])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[N:18]=[C:19]([CH:22]=O)[S:20][CH:21]=3)[CH:15]=2)[N:10]([C:24](=[O:26])[CH3:25])[C@@H:9]([CH3:27])[CH2:8]1)[CH3:3].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:24]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:18]=[C:19]([CH2:22][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[S:20][CH:21]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:28])[O:4][CH:2]([CH3:3])[CH3:1])[CH2:8][C@@H:9]1[CH3:27])(=[O:26])[CH3:25]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 866692321-Methylethyl [(cis)-1-acetyl-6-(2-formyl-1,3-thiazol-4-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

생성물 1

HCID 866692631-Methylethyl {(cis)-1-acetyl-2-methyl-6-[2-(1-piperidinylmethyl)-1,3-thiazol-4-yl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-Methylethyl[(cis)-1-acetyl-6-(2-formyl-1,3-thiazol-4-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 39) (21 mg, 0.052 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with piperidine (7.77 μL, 0.078 mmol) and acetic acid (7.49 μL, 0.131 mmol) and stirred under nitrogen for 30 minutes. Sodium triacetoxyborohydride (16.63 mg, 0.078 mmol) was added and the mixture was allowed to stir under nitrogen. The mixture was loaded onto a 2 g SCX-column, eluting with MeOH (25 mL) followed by 2M MeOH/NH3 (25 mL). Product-containing fractions were evaporated to dryness to give a solid (18 mg). This was purified on a 12+M Biotage silica column, eluting with 0 to 4% 2N methanolic ammonia in DCM. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (16 mg).

후처리

  1. stirringto stir under nitrogen
  2. washeluting with MeOH (25 mL)
  3. customProduct-containing fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-3ffc1b80930c4cc18a2348ce31ed3021
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697725B2

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