1,1'-Carbonyldiimidazole → HCID 86726342, 화합물

HRID 629742노트

반응식

HRID 629742 반응식
C(OC(N[C@H:9]([C:25]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([F:51])[C:33]=1[CH2:34][CH2:35][C@H:36]1[O:41][CH2:40][C@@H:39]([CH2:42][OH:43])[N:38](C(OC(C)(C)C)=O)[CH2:37]1)=[O:26])[CH:10]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O)(C)(C)C.[C:52](N1C=CN=C1)(N1C=CN=C1)=[O:53].[Cl:64][C:65]1[N:70]=[C:69]([CH2:71][NH2:72])[CH:68]=[CH:67][CH:66]=1>N1C=CC=CC=1>[Cl:64][C:65]1[N:70]=[C:69]([CH2:71][NH:72][C:52](=[O:53])[O:43][CH2:42][C@@H:39]2[CH2:40][O:41][C@H:36]([CH2:35][CH2:34][C:33]3[C:32]([F:51])=[CH:31][N:30]=[CH:29][C:28]=3[NH:27][C:25](=[O:26])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:37][NH:38]2)[CH:68]=[CH:67][CH:66]=1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10313191(6-Chloropyridin-2-yl)methanamineHCID 86726337HCID 86726337, 화합물

생성물 1

HCID 86726342HCID 86726342, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
60 °C

실험 절차

To a mixture of tert-Butyl (2R,5R)-2-[2-(3-{[N-(tert-butoxycarbonyl)-4-fluoro-β-(4-fluorophenyl)-L-phenylalanyl]amino}-5-fluoropyridin-4-yl)ethyl]-5-(hydroxymethyl)morpholine-4-carboxylate (Example 149, Step 7) (677 mg, 0.95 mmol) and carbonyldiimidazole (154 mg, 0.95 mmol) was added dry pyridine (22.5 mL). The resulting solution was heated at 60° C. and stirred for 2 h. This solution was then distributed in 0.5 mL (0.021 mmol) aliquots to 45 2-dram sample vials, each containing a diverse amine (0.042 mmol); among them (6-chloropyridin-2-yl)methanamine. The resulting mixtures were stirred at 60° C. for 3 h. Solvent was removed under stream of N2 gas. The residues were diluted with 4 N HCl/diethyl ether (1 mL) and stirred at room temperature for 16 h. Solvent was removed under stream of N2 gas, and the residues were diluted with DMSO and purified by mass-guided reversed-phase HPLC (10-90% CH3CN:0.1% NH4OH/H2O). HRMS (ES) 683.2353 (M+H). found, 683.2355 required.

후처리

  1. stirringThe resulting mixtures were stirred at 60° C. for 3 h
  2. customSolvent was removed under stream of N2 gas
  3. additionThe residues were diluted with 4 N HCl/diethyl ether (1 mL)
  4. stirringstirred at room temperature for 16 h
  5. customSolvent was removed under stream of N2 gas
  6. additionthe residues were diluted with DMSO
  7. custompurified by mass-guided reversed-phase HPLC (10-90% CH3CN:0.1% NH4OH/H2O)

출처 및 근거

ORD 기록
ord-2446a8c255c64da9916cf6108b50807f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315475B2

반응 노트

불러오는 중…