Acetic Acid → HCID 86700267, compound

HRID 879457Notes

Reaction equation

HRID 879457 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:33]([CH3:34])=[N:32][N:31]([CH3:35])[C:28]5=[CH:29][N:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=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:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:33]([CH3:34])=[N:32][N:31]([CH3:35])[C:28]5=[CH:29][N:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 86700265HCID 86700265, compound

Product 1

HCID 86700267HCID 86700267, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1,3-dimethyl-1H-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (5.6 mg, 0.009 mmol)and 5M NaOH (0.035 mL, 0.175 mmol) in MeOH (0.1 mL) and THF (0.5 mL) was stirred at 50° C. for 3 hours, then stored in freezer overnight. DMF (0.3 mL) and acetic acid (0.011 mL) 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 desired product. LCMS-ESI+: calc'd for C33H31ClN5O3S: 612.2 (M+H+); Found: 612.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 7.95 (s, 2H), 7.8-7.6 (m, 8H), 5.26 (s, 1H), 4.13 (s, 3H), 2.69 (s, 3H), 2.64 (s, 3H), 0.97 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-bc92bdc7602d4f0d90b8efc38c894f0e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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