Acetonitrile → Methyl 2-[N-(tert-Butoxycarbonyl)-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate

HRID 1831013Notes

Reaction equation

HRID 1831013 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:37]=[CH:36][C:33]([C:34]#N)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(#[N:46])C>>[C:1]([O:5][C:6]([N:8]([C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH2:34][C:33]1[CH:36]=[CH:37][C:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]#[N:46])=[CH:31][CH:32]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoateHCID 154871552'-(Bromomethyl)[1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 10874596Methyl 2-[N-(tert-Butoxycarbonyl)-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate

Conditions

Temperature
82.5 °C

Procedure

Methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] obtained in Reference Example 3 (354 kg), a solution of 4-(2-bromomethylphenyl)benzonitrile [BMB] in acetonitrile obtained in Reference Example 4 (1), and anhydrous potassium carbonate (475 kg) were added to acetonitrile (1600 kg), and the mixture was heated (80 to 85° C.) under reflux for about 5 hours. The reaction solution was cooled, and the insoluble were separated and washed with acetonitrile (320 kg). The filtrated washing was concentrated under reduced pressure to give concentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2′-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].

Workup

  1. temperatureunder reflux for about 5 hours
  2. temperatureThe reaction solution was cooled
  3. customthe insoluble were separated
  4. washwashed with acetonitrile (320 kg)
  5. washThe filtrated washing
  6. concentrationwas concentrated under reduced pressure
  7. customto give
  8. concentrationconcentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2′-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN]

Sources & evidence

ORD record
ord-3476f512d8cb451990d00c11912af97f
Source dataset
uspto-grants-2006_06
Patent number
US07067546B2

Reaction notes

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