Water → HCID 18470834, compound

HRID 2228742Notes

Reaction equation

HRID 2228742 reaction equation
FC(F)(F)[C:3]([N:5](C)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][NH:15][C:16]2[C:21](=[O:22])[N:20]([CH2:23][C:24]([NH:26][CH2:27][C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[NH:33][CH:32]=[C:31]4[CH3:37])=[O:25])[C:19]([CH3:38])=[CH:18][N:17]=2)[CH:8]=1)=O.C([O-])([O-])=O.[Na+].[Na+].O>CO>[CH3:37][C:31]1[C:30]2[C:34](=[CH:35][CH:36]=[C:28]([CH2:27][NH:26][C:24](=[O:25])[CH2:23][N:20]3[C:19]([CH3:38])=[CH:18][N:17]=[C:16]([NH:15][CH2:14][CH2:13][C:9]4[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][NH:5][CH3:3])[CH:8]=4)[C:21]3=[O:22])[CH:29]=2)[NH:33][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 18470790HCID 18470790, compound

Product 1

HCID 18470834HCID 18470834, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,2,2-Trifluoro-N-methyl-N-[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]acetamide (preparation 38) (40 mg, 0.07 mmol) was dissolved in hot methanol (15 ml) and treated with an aq. solution of Na2CO3 (0.6 ml, 0.46 mol) followed by an additional portion of water (1.5 ml). The resultant cloudy mixture was stirred at room temperature for 18 hr, then evaporated to dryness and dried. The resultant white solid was purified by chromatography (SiO2, gradient elution with 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3) to give the desired product (34 mg, 100%). 1H NMR (CDCl3) δ 2.15 (s, 3H), 2.30 (s, 3H), 2.50 (s, 3H), 2.90 (t, 2H), 3.60 (t, 2H), 3.90 (s, 2H), 4.50 (s, 2H), 4.75 (s, 2H), 6.70 (s, 1H), 7.00 (s, 1H), 7.05 (d, 1H), 7.20-7.40 (m, 5H), 7.45 (s, 1H). LRMS m/z=473.4 (M+1)+.

Workup

  1. customevaporated to dryness
  2. customdried
  3. customThe resultant white solid was purified by chromatography (SiO2, gradient elution with 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3)

Sources & evidence

ORD record
ord-70dea9a08e32415d9aaef73f864572a7
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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