Hydrochloric Acid → tert-Butyl 2-{[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]oxy}ethylcarbamate

HRID 567848Notes

Reaction equation

HRID 567848 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH2:16][CH2:17][NH:18][C:19]1[C:20](=[O:30])[N:21]([CH2:26][C:27]([OH:29])=O)[C:22]([CH3:25])=[CH:23][N:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([CH2:44][NH2:45])[CH:42]=2)[NH:37][CH:36]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN1CCOCC1>CN(C)C=O>[CH3:25][C:22]1[N:21]([CH2:26][C:27]([NH:45][CH2:44][C:41]2[CH:42]=[C:43]3[C:38](=[CH:39][CH:40]=2)[NH:37][CH:36]=[C:35]3[CH3:34])=[O:29])[C:20](=[O:30])[C:19]([NH:18][CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([CH:33]=[CH:32][CH:31]=2)[CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[N:24][CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 184709262-[3-{[3-({2-[(tert-Butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

Product 1

HCID 18470880tert-Butyl 2-{[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]oxy}ethylcarbamateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[3-{[3-({2-[(tert-butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino)6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (preparation 107) (174 mg, 0.38 mmol), (3-methyl-1H-indol-5-yl)methylamine (preparation 36) (67 mg, 0.42 mmol), HOBT (77 mg, 0.57 mmol), WSCDI.HCl (91 mg, 0.47 mmol) and N-methylmorpholine (124 ml, 1.13 mmol) in N,N-dimethylformamide (5 ml), was stirred at room temperature for 20 hrs. The reaction mixture was partitioned between ethyl acetate and water and the .phases separated. The organic layer was dried over MgSO4 and evaporated under reduced pressure to give the title compound as a white solid, (220 mg, 96%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe .phases separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6ba5998538854db4a56e31bb892884a5
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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