Diphenyl N-Cyanocarbonimidate → HCID 178512285、化合物

HRID 1919473ノート

反応式

HRID 1919473 の反応式
C1C=CC(O[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]#[N:11])=CC=1.[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)(C)C>[C:10](/[N:9]=[C:8](\[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)/[NH:31][C:30]1[CH:32]=[CH:33][C:27]([O:26][CH2:25][CH2:24][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:28][CH:29]=1)#[N:11]

参加物

4

反応物 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

生成物 1

HCID 178512285HCID 178512285、化合物

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Diphenylcyanocarbonimidate (1.1 equiv) and 4-(2-(pyrrolidin-1-yl)ethoxy)aniline (1 equiv) were stirred in iso-propyl alcohol at ambient temperature overnight. The resulting white precipitate was filtered and washed with iso-propyl alcohol and dried to yield (Z)-phenyl N′-cyano-N-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)carbamimidate. 3-Hydrazino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazine (82 mg, 0.36 mMol) and (Z)-phenyl N′-cyano-N-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)carbamimidate (128 mg, 0.36 mMol) were suspended in isopropanol (3 mL) and subjected to microwave irradiation (150° C., 20 min). The precipitate which formed in the microwave vial was re-dissolved in hot isopropanol. The mixture was cooled to ambient temperature and then filtered to give 1-(6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3-yl)-N3-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-1H-1,2,4-triazole-3,5-diamine, compound #1, as a yellow solid, 23 mg. 1H NMR (CDCl3, 300 MHz) 7.90 (s, 1H), 7.83 (t, 1H), 7.43 (m, 3H), 7.29 (t, 1H), 6.93 (d, 1H), 6.83 (br s, 2H), 6.39 (s, 1H), 4.17 (m, 2H), 2.98 (m, 2H), 2.60-2.80 (m, 8H), 2.32 (m, 2H), 1.87 (m, 4H) ppm; MS (ES) 483.16 (M+H).

後処理

  1. filtrationThe resulting white precipitate was filtered
  2. washwashed with iso-propyl alcohol
  3. customdried

出典と根拠

ORDレコード
ord-448891e46b9943299156257cf9596b75
出典データセット
uspto-grants-2012_05
特許番号
US08168636B2

反応ノート

読み込み中…