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 1046977ノート

反応式

HRID 1046977 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-b9a791922c0846de989ee1797c608944
出典データセット
uspto-grants-2013_10
特許番号
US08569331B2

反応ノート

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