Acetic Acid → HCID 72195977, compound

HRID 879451Notes

Reaction equation

HRID 879451 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:35]([CH3:36])=[CH:34][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N:25]4[CH:30]=[C:29]([CH3:31])[C:28](=[O:32])[NH:27][C:26]4=[O:33])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CN(C=O)C.C(O)(=O)C>CO.C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:35]([CH3:36])=[CH:34][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N:25]4[CH:30]=[C:29]([CH3:31])[C:28](=[O:32])[NH:27][C:26]4=[O:33])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 86700259HCID 86700259, compound

Product 1

HCID 72195977HCID 72195977, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)phenyl)benzo[d]thiazol-6-yl)acetate (12.9 mg, 0.0212 mmol) and 5M NaOH (85 μL, 0.424 mmol) in MeOH (0.1 mL) and THF (1.2 mL) was stirred at 50° C. for 1.5 hours. DMF (0.3 mL) and acetic acid (75 μL) were added and reaction mixture was concentrated to ˜0.3 mL, filtered using a syringe filter, diluted with methanol. Purified using Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) and lyophilized to give product. LCMS-ESI+: calc'd for C31H29ClN3O5S: 590.1 (M+H+); Found: 590.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.07 (d, J=8.5 Hz, 1H), 7.94 (dd, J=1.8, 1.8 Hz, 1H), 7.84 (s, 1H), 7.71-7.47 (m, 5H), 7.43-7.22 (m, 2H), 5.25 (s, 1H), 2.60 (s, 3H), 1.92 (d, J=5.2 Hz, 3H), 1.34 (s, 3H), 0.96 (s, 9H).

Workup

  1. customreaction mixture
  2. concentrationwas concentrated to ˜0.3 mL
  3. filtrationfiltered
  4. filtrationfilter
  5. additiondiluted with methanol
  6. customPurified
  7. customto give product

Sources & evidence

ORD record
ord-9b3a55e5997c4da5a1b69c6f11bfa860
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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