Acetic Acid → HCID 86700252, compound

HRID 879443Notes

Reaction equation

HRID 879443 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:33]=[C:32]5[C:28]([C:29]([F:35])=[N:30][N:31]5[CH3:34])=[CH:27][CH:26]=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:33]=[C:32]5[C:28]([C:29]([F:35])=[N:30][N:31]5[CH3:34])=[CH:27][CH:26]=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]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 86700251HCID 86700251, compound

Product 1

HCID 86700252HCID 86700252, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3-fluoro-1-methyl-1H-indazol-6-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (37 mg, 0.058 mmol) and 5M NaOH (0.23 mL, 1.15 mmol) in MeOH (0.5 mL) and THF (2 mL) was stirred at 45° C. for 2 hours. DMF (0.3 mL) and acetic acid (73 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 C33H29ClFN4O3S: 615.2 (M+H+); Found: 615.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.80 (d, J=5.4 Hz, 1H), 8.58 (s, 1H), 8.20 (s, 1H), 8.02 (dd, J=5.3, 1.6 Hz, 1H), 7.95 (s, 1H), 7.83 (dd, J=28.4, 8.6 Hz, 2H), 7.76-7.67 (m, 1H), 7.60 (br s, 3H), 5.28 (s, 1H), 4.01 (s, 3H), 2.64 (s, 3H), 0.98 (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-55201c43b1f145bc841d03abfc3dcabc
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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