Cyclopropylamine → 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-4-methylbenzamide

HRID 337105Notes

Reaction equation

HRID 337105 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH:19][C:20]2[C:21](=[O:38])[N:22]([C:27]3[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=3[CH3:37])[C:30]([O:32]C)=O)[CH:23]=[C:24]([Br:26])[N:25]=2)[CH2:18][CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:39]1([NH2:42])[CH2:41][CH2:40]1.C([Mg]Cl)(C)C>C1COCC1.[Cl-].[NH4+]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH:19][C:20]2[C:21](=[O:38])[N:22]([C:27]3[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=3[CH3:37])[C:30]([NH:42][CH:39]3[CH2:41][CH2:40]3)=[O:32])[CH:23]=[C:24]([Br:26])[N:25]=2)[CH2:18][CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 66689709Methyl 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoateHCID 178418918HCID 178418918, compound

Product 1

HCID 666896093-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of methyl 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate (Example 268d, 1.46 g) in THF (40 mL) under nitrogen was treated with cyclopropylamine (0.88 mL) followed by isopropylmagnesium chloride (3.81 mL, 2.0 M in THF) dropwise over 10 min. The reaction was stirred at room temperature for 1 h then diluted with saturated aqueous ammonium chloride solution (300 mL) and extracted with ethyl acetate (×3). The combined organics were dried (MgSO4), filtered and evaporated to afford the subtitle product (1.537 g).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8f5d98cd944b4fbe8ecff76809658003
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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