Diphenyl N-Cyanocarbonimidate → HCID 178512285, compound

HRID 1919473Notes

Reaction equation

HRID 1919473 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 178512285HCID 178512285, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-448891e46b9943299156257cf9596b75
Source dataset
uspto-grants-2012_05
Patent number
US08168636B2

Reaction notes

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