1,1'-Thiocarbonyldiimidazole → HCID 59464031, compound

HRID 1713787Notes

Reaction equation

HRID 1713787 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:16](N1C=CN=C1)(N1C=CN=C1)=S.[NH:28]([C:30](=[O:50])[C:31]([NH:33][C:34]1[CH:35]=[CH:36][C:37]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([O:48][CH3:49])=[O:47])[CH2:42][CH2:41]2)=[N:38][CH:39]=1)=[O:32])[NH2:29].CCN=C=NCCCN(C)C.Cl>CC(N(C)C)=O.O>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:16]3[O:50][C:30]([C:31]([NH:33][C:34]4[CH:35]=[CH:36][C:37]([N:40]5[CH2:41][CH2:42][CH:43]([C:46]([O:48][CH3:49])=[O:47])[CH2:44][CH2:45]5)=[N:38][CH:39]=4)=[O:32])=[N:28][N:29]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 147633Benzenamine, 4-(4-fluorophenoxy)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68683563HCID 68683563, compound

Product 1

HCID 59464031HCID 59464031, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of 4-(4-fluorophenoxy)aniline (190 mg, 0.93 mmol) in anhydrous DMA (4 mL) was added 1,1′-carbonothioylbis(1H-imidazole) (167 mg, 0.93 mmol) and the mixture stirred at ambient temperature for 1 hr. Methyl 1-(5-{[hydrazino(oxo)acetyl]amino}pyridin-2-yl)piperidine-4-carboxylate (250 mg, 0.78 mmol) was added and the reaction mixture was heated to 50° C. for 1 hr. EDCI.HCl (180 mg, 0.93 mmol) was added and the reaction mixture heated to 85° C. overnight and then allowed to cool to ambient temperature. Water (˜20 mL) was added and the suspension filtered, washed with ether (˜15 mL) and dried to leave the title compound as a pale yellow solid (415 mg, 0.780 mmol, 100%). 1H NMR δ 1.50-1.58 (m, 2H), 1.87-1.90 (m, 2H), 2.61-2.67 (m, 1H), 2.90-2.94 (m, 2H), 3.62 (s, 3H), 4.17 (d, 2H), 6.87-6.89 (m, 1H), 7.00-7.10 (m, 4H), 7.19-7.23 (m, 2H), 7.60-7.63 (m, 2H), 7.90-7.92 (m, 1H), 8.48 (s, 1H), 10.95 (s, 1H), 10.99 (s, 1H); MS m/e MH+ 533.

Workup

  1. temperaturethe reaction mixture was heated to 50° C. for 1 hr
  2. temperaturethe reaction mixture heated to 85° C. overnight
  3. temperatureto cool to ambient temperature
  4. filtrationthe suspension filtered
  5. washwashed with ether (˜15 mL)
  6. customdried

Sources & evidence

ORD record
ord-23f99872e07b44cb95cf5c14b3b1f2bb
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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