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Phenyl 5-cyanopyrazin-2-ylcarbamate → tert-Butyl 2-(2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)phenoxy)ethyl(2,4-difluorobenzyl)carbamate

HRID 1019739
Notes
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Reaction equation

HRID 1019739 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([Cl:28])[CH:3]=1.[C:29]([C:31]1[N:32]=[CH:33][C:34]([NH:37][C:38](=O)[O:39]C2C=CC=CC=2)=[N:35][CH:36]=1)#[N:30]>CN(C)C=O>[Cl:28][C:4]1[CH:3]=[C:2]([NH:1][C:38]([NH:37][C:34]2[CH:33]=[N:32][C:31]([C:29]#[N:30])=[CH:36][N:35]=2)=[O:39])[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][CH2:8][N:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 22064357Phenyl 5-cyanopyrazin-2-ylcarbamateHCID 67469270tert-Butyl 2-(4-amino-2-chlorophenoxy)ethyl(2,4-difluorobenzyl)carbamate

Product 1

HCID 67469007tert-Butyl 2-(2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)phenoxy)ethyl(2,4-difluorobenzyl)carbamateYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 2-(4-amino-2-chlorophenoxy)ethyl(2,4-difluorobenzyl)-carbamate (1.6 g, 3.87 mmol) in N,N-dimethylformamide (4 mL) at RT were phenyl 5-cyanopyrazin-2-ylcarbamate (1.39 g, 5.81 mmol) (Example 10) and N,N,N-diisopropylethylamine (0.751 g, 5.81 mmol) added. The reaction mixture was heated at 60° C. for 1.5 hours then the reaction mixture was poured into ice-water (100 mL) and allowed to stand for 30 minutes. The resulting precipitate was collected, washed with water and air dried. The crude product was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM to give the title compound (0.53 g, 26% yield).

Workup

  1. customat RT
  2. additionadded
  3. customThe resulting precipitate was collected
  4. washwashed with water and air
  5. customdried
  6. customThe crude product was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM

Sources & evidence

ORD record
ord-a9169ecee8d54eac94e7e15b2504a5bc
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716287B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes