Dimethylformamide → HCID 86700240, compound

HRID 879433Notes

Reaction equation

HRID 879433 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][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][N:28]([CH2:31][CH3:32])[CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C1COCC1.CN(C=O)C>CO.C(O)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH2:30]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86700239HCID 86700239, compound

Product 1

HCID 86700240HCID 86700240, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-ethylpiperazin-1-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (26.7 mg, 0.044 mmol), 5M NaOH (176 μL, 0.879 mmol)) in methanol (0.2 mL) and THF (1.0 mL) was stirred at 45° C. for 2 h, then stirred overnight at rt. Acetic acid (1 drop) and DMF (0.3 mL) were added and mixture concentrated to ˜0.3 mL, diluted with methanol, 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 C31H36ClN4O3S: 579.2 (M+H+); Found: 579.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.27 (d, J=5.4 Hz, 1H), 7.84 (s, 1H), 7.66 (dd, J=8.5, 1.7 Hz, 1H), 7.63-7.52 (m, 3H), 7.50 (s, 1H), 7.32 (dd, J=5.4, 1.3 Hz, 1H), 5.25 (s, 1H), 4.81-4.18 (m, 2H), 4.81-4.18 (m, 2H), 3.7-2.99 (m, 4H), 3.27 (dd, J=14.8, 7.5 Hz, 3H), 2.59 (s, 3H), 1.39 (t, J=7.3 Hz, 3H), 0.96 (s, 9H).

Workup

  1. concentrationmixture concentrated to ˜0.3 mL
  2. additiondiluted with methanol
  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-caec59151c2648e4add44a0365399147
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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