Hydrochloric Acid → HCID 59900516, compound

HRID 2228796Notes

Reaction equation

HRID 2228796 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:33]=[CH:34][CH:35]=1)[CH2:18][CH2:19][NH:20][C:21]1[C:22](=[O:32])[N:23]([CH2:28][C:29](O)=[O:30])[C:24]([CH3:27])=[CH:25][N:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([CH2:46][NH2:47])[CH:44]=2)[NH:39][CH:38]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN1CCOCC1>CN(C)C=O>[CH3:27][C:24]1[N:23]([CH2:28][C:29]([NH:47][CH2:46][C:43]2[CH:44]=[C:45]3[C:40](=[CH:41][CH:42]=2)[NH:39][CH:38]=[C:37]3[CH3:36])=[O:30])[C:22](=[O:32])[C:21]([NH:20][CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH:35]=[CH:34][CH:33]=2)[O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[N:26][CH:25]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 70052853HCID 70052853, compound

Product 1

HCID 59900516HCID 59900516, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[3-[(3-{[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]methoxy}phenethyl)amino]-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (preparation 136) (65 mg, 0.13 mmol), (3-methyl-1H-indol-5-yl)methylamine (preparation 36) (25 mg, 0.16 mmol), HOBT (20 mg, 0.15 mmol), WSCDl.HCl (31 mg, 0.16 mmol) and N-methylmorpholine (40 mg, 0.40 mmol) in N,N-dimethylformamide (2.5 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 washed with water, brine, then dried over MgSO4 and evaporated under reduced pressure to give the title compound, (84 mg, 100%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe phases separated
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f59b9a9aeb7843e5bbd01b2102e0d081
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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