Hydrochloric Acid → 1-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine

HRID 1046977노트

반응식

HRID 1046977 반응식
[CH2:1]([C:9]1[N:10]=[C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][C:14]3[N:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]2[C:26]=1[C:27]1[CH:32]=[CH:31][C:30]([C:33]2([NH:37]C(=O)OC(C)(C)C)[CH2:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>ClCCl.O1CCOCC1>[CH2:1]([C:9]1[N:10]=[C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][C:14]3[N:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]2[C:26]=1[C:27]1[CH:32]=[CH:31][C:30]([C:33]2([NH2:37])[CH2:34][CH2:35][CH2:36]2)=[CH:29][CH:28]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 136331867tert-butyl (1-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate

생성물 1

HCID 1363902441-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of tert-butyl (1-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate (0.042 g) in dichloromethane (2 mL) was added 4.0 M HCl in dioxane (0.18 mL). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was treated with aq. saturated sodium bicarbonate (10 mL). The mixture was extracted with dichloromethane (2×10 mL). The combined extracts were concentrated under reduced pressure and the crude product was purified by preparative HPLC (YMC PACK ODS-AM; AM12S05-1020WT; 100×20 mm ID; CAN/0.1% TFA, 30 mL/min) The product, 1-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine was obtained as a yellow solid (0.010 g, 29%). M.p.: 158-160° C.; 1H NMR (DMSO-d6) 400 MHz δ 8.62 (br. s, 1 H), 8.56 (br. s, 3H), 8.12 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 7.91 (dd, JA=7.6 Hz, JB=1.6 Hz, 1H), 7.48 (d, J=8.4 Hz, 2H), 7.40-7.36 (m, 1H), 7.32-7.22 (m, 3H), 7.21-7.05 (m, 6H), 6.82 (dd, JA=8.0 Hz, JB=1.6 Hz, 1H), 6.76 (dd, JA=7.6 Hz, JB=4.0 Hz, 1H), 3.05-2.97 (m, 2H), 2.91-2.83 (m, 2H), 2.64-2.46 (m, 4H), 2.22-2.10 (m, 1H), 1.87-1.75 (m, 1H); LCMS: 484 [M+H].

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with aq. saturated sodium bicarbonate (10 mL)
  3. extractionThe mixture was extracted with dichloromethane (2×10 mL)
  4. concentrationThe combined extracts were concentrated under reduced pressure
  5. customthe crude product was purified by preparative HPLC (YMC PACK ODS-AM; AM12S05-1020WT; 100×20 mm ID; CAN/0.1% TFA, 30 mL/min) The product

출처 및 근거

ORD 기록
ord-b9a791922c0846de989ee1797c608944
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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