Dimethylformamide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879429Notes

Reaction equation

HRID 879429 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C>CO.C1COCC1.C(O)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86700235(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700234(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate (4.2 mg, 0.00724 mmol) 5M NaOH (29 μL) in methanol (0.2 mL) and THF (1.0 mL) was stirred at 40° C. overnight. Acetic acid (1 drop) and DMF (0.3 mL) were added and mixture concentrated to ˜0.5 mL, diluted with DMF/H2O, filtered and purified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to give product after lyophilization. LCMS-ESI+: calc'd for C29H31ClN3O4S: 552.2 (M+H+); Found: 552.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.12 (d, J=6.2 Hz, 1H), 7.94 (s, 1H), 7.69 (s, 1H), 7.67 (d, J=2.1 Hz, 1H), 7.61 (d, J=2.1 Hz, 1H), 7.59 (dd, J=4.2, 2.1 Hz, 2H), 7.47 (dd, J=6.2, 1.5 Hz, 1H), 5.26 (s, 1H), 3.91-3.79 (m, 4H), 3.74-3.62 (m, 4H), 2.63 (s, 3H), 0.97 (s, 9H).

Workup

  1. concentrationmixture concentrated to ˜0.5 mL
  2. additiondiluted with DMF/H2O
  3. filtrationfiltered
  4. custompurified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)
  5. customto give product after lyophilization

Sources & evidence

ORD record
ord-6e8cb02d63074d6686997f35ecee8086
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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