Hydrochloric Acid → HCID 59900604, compound

HRID 2228786Notes

Reaction equation

HRID 2228786 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([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)[CH2:10][O:11][CH3:12])=[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.O>[CH3:12][O:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:13]1[CH:33]=[CH:32][CH:31]=[C:15]([CH2:16][CH2:17][NH:18][C:19]2[C:20](=[O:30])[N:21]([CH2:26][C:27]([NH:45][CH2:44][C:41]3[CH:42]=[C:43]4[C:38](=[CH:39][CH:40]=3)[NH:37][CH:36]=[C:35]4[CH3:34])=[O:29])[C:22]([CH3:25])=[CH:23][N:24]=2)[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 18470813(3-methyl-1H-indol-5-yl)methanamine2×HCID 59900557HCID 59900557, compound

Product 1

HCID 59900604HCID 59900604, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[3-[(3-{(1R/S)-1-[(tert-butoxycarbonyl)amino]-2-methoxyethyl}phenethyl)amino]-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (preparation 123) (35 mg, 0.076 mmol), (3-methyl-1H-indol-5-yl)methylamine (preparation 36) (13 mg, 0.08 mmol), HOBT (11 mg, 0.08 mmol), WSCDl.HCl (16 mg, 0.08 mmol) and N-methylmorpholine (16 ml, 0.15 mmol) in N,N-dimethylformamide (2 ml), was stirred at room temperature for 18 hrs. Additional (3-methyl-1H-indol-5-yl)methylamine (preparation 36) (8 mg, 0.038 mmol), was added, and stirring continued for a further 72 hrs at room temperature. The reaction mixture was poured into water (10 ml), and the resulting precipitate filtered, and dried to give the desired product, (26 mg, 57%).

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-ba93b3406f0745b29e8a67d6ad574649
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

Loading…