Ammonia → HCID 86721459, compound

HRID 869604Notes

Reaction equation

HRID 869604 reaction equation
[C:1](/[C:3](=[C:5]1/[C:6]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[N:21]4[CH:22]=[CH:23][C:24]([C:26](O)=[O:27])=[CH:25][C:20]4=[N:19][C:18]=3[CH:29]3[CH2:31][CH2:30]3)[CH:13]=[CH:12][C:11]/1=2)/[CH3:4])#[N:2].C(N1C=CN=C1)([N:39]1C=CN=C1)=O.N.Cl>C1COCC1>[C:1](/[C:3](=[C:5]1/[C:6]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[N:21]4[CH:22]=[CH:23][C:24]([C:26]([NH2:39])=[O:27])=[CH:25][C:20]4=[N:19][C:18]=3[CH:29]3[CH2:31][CH2:30]3)[CH:13]=[CH:12][C:11]/1=2)/[CH3:4])#[N:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 86721457HCID 86721457, compound

Product 1

HCID 86721459HCID 86721459, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

[step 6] (E)-3-{[11(6H)-(1-cyanoethylidene)-3-fluorodibenzo[b,e]oxepin-8-yl]methyl}-2-cyclopropylimidazo[1,2-a]pyridine-7-carboxylic acid (2.4 g, 5.1 mmol) obtained in step 5 was suspended in THF (25 mL), 1,1′-carbonyldiimidazole (4.1 g, 25 mmol) was added, and the mixture was stirred with heating at 60° C. for 1.5 hr. To the reaction mixture was added 25% aqueous ammonia solution (4.4 mL, 51 mmol), and the mixture was stirred at room temperature for 15 min. To the mixture was added 2 mol/L hydrochloric acid, and the mixture was stirred at room temperature for 1.5 hr. The precipitated crystals were collected by suction filtration, and dried at 50° C. under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-10/90 v/v) to give the title compound (2.1 g, 86%).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. stirringthe mixture was stirred at room temperature for 1.5 hr
  3. filtrationThe precipitated crystals were collected by suction filtration
  4. customdried at 50° C. under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-10/90 v/v)

Sources & evidence

ORD record
ord-40409d4cae44415099f1599e1b6edf8a
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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