Hydrochloric Acid → N-Cyclopropyl-2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzamide

HRID 1697400Notes

Reaction equation

HRID 1697400 reaction equation
C([Mg]Cl)(C)C.[CH:6]1([NH2:9])[CH2:8][CH2:7]1.[F:10][C:11]1[CH:20]=[C:19]([CH3:21])[C:18]([N:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]3([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[OH:38])[CH2:31][CH2:30]3)[C:23]2=[O:39])=[CH:17][C:12]=1[C:13](OC)=[O:14].Cl>C1COCC1.O>[CH:6]1([NH:9][C:13](=[O:14])[C:12]2[CH:17]=[C:18]([N:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]4([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[OH:38])[CH2:31][CH2:30]4)[C:23]3=[O:39])[C:19]([CH3:21])=[CH:20][C:11]=2[F:10])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 66689715methyl 2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzoateHCID 178418918HCID 178418918, compound

Product 1

HCID 66689387N-Cyclopropyl-2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropylmagnesium chloride (5.19 mL of a 2.0 M solution in THF) was added over 20 min of a solution of cyclopropylamine (1.830 mL) and methyl 2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzoate (Example 318f, 1.063 g) in THF (20 mL) stirring at room temperature under nitrogen. The reaction mixture was stirred for 1 h. Water and 2 M HCl were cautiously added and the volatiles removed in vacuo. The residue was basified with saturated aqueous sodium bicarbonate solution and extracted into DCM. The organics were combined, dried (MgSO4) and evaporated to give the subtitle compound (1.189 g).

Workup

  1. stirringThe reaction mixture was stirred for 1 h
  2. customthe volatiles removed in vacuo
  3. extractionextracted into DCM
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c03426e0aab44f21b6f05fef37e9513f
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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