Diphenyl N-Cyanocarbonimidate → HCID 178512285, 화합물

HRID 2233132노트

반응식

HRID 2233132 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 178512285HCID 178512285, 화합물

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9cd49a57003c4f4cb6e516f3c5c1a877
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709482B2

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