Water → HCID 18470834, compound

HRID 567816Notes

Reaction equation

HRID 567816 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-0627396f230c4c8ea50f3bc4947d5d79
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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