Hydrochloric Acid → N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine

HRID 1186539ノート

反応式

HRID 1186539 の反応式
C(OC(=O)[NH:7][CH2:8][CH:9]([NH:15][C:16]1[N:21]=[C:20]([C:22]2[N:26]3[CH:27]=[CH:28][N:29]=[C:30]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[C:25]3=[N:24][CH:23]=2)[CH:19]=[CH:18][N:17]=1)[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)(C)(C)C.Cl>C(O)C>[CH3:37][N:34]1[CH2:33][CH2:32][N:31]([C:30]2[C:25]3[N:26]([C:22]([C:20]4[CH:19]=[CH:18][N:17]=[C:16]([NH:15][CH:9]([C:10]5[CH:14]=[CH:13][S:12][CH:11]=5)[CH2:8][NH2:7])[N:21]=4)=[CH:23][N:24]=3)[CH:27]=[CH:28][N:29]=2)[CH2:36][CH2:35]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 68226841(2-{4-[8-(4-Methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester

生成物 1

HCID 66546330N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of crude (2-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester (150 mg, 0.280 mmol) in ethanol (5 mL) was added concentrated hydrochloric acid (5 mL) slowly. The reaction mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and then the solid was purified by prep-HPLC. Several drops of concentrated HCl were added to the fractions with product. After sonicating for several minutes, solution was concentrated under reduced pressure to afford N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine; hydrochloride. (Yield 13 mg, 5.57%). 1H NMR (300 MHz, CD3OD): δ 8.81 (brs, 1H), 8.63 (s, 1H), 8.29 (d, 1H, J=6.0 Hz), 7.61-7.52 (m, 3H), 7.46-7.43 (m, 1H), 7.23 (d, 1H, J=5.1 Hz), 5.72 (brs, 1H), 5.47-5.43 (m, 2H), 3.63-3.60 (m, 4H), 3.50-3.48 (m, 2H), 3.29-3.26 (m, 2H), 2.89 (s, 3H). LC-MS: [M+H]+ 436.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe solid was purified by prep-HPLC
  3. additionSeveral drops of concentrated HCl were added to the fractions with product
  4. customAfter sonicating for several minutes
  5. concentrationsolution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-35d65739f2e94d1f94806a9b54541d5d
出典データセット
uspto-grants-2014_03
特許番号
US08673905B2

反応ノート

読み込み中…