Dimethylformamide → HCID 86700242, compound

HRID 879435Notes

Reaction equation

HRID 879435 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][N:22]=[C:21]([N:25]4[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]4)[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+].C1COCC1.CN(C=O)C>CO.C(O)(=O)C>[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][N:22]=[C:21]([N:25]4[CH2:30][CH2:29][N:28]([CH:31]([CH3:32])[CH3:33])[CH2:27][CH2:26]4)[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])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86700241HCID 86700241, compound

Product 1

HCID 86700242HCID 86700242, 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-isopropylpiperazin-1-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (36.7 mg, 0.059 mmol), 5M NaOH (236 μL, 1.18 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 DMF/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 C32H38ClN4O3S: 593.2 (M+H+); Found: 593.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.26 (d, J=5.5 Hz, 1H), 7.84 (s, 1H), 7.66 (dd, J=8.5, 1.8 Hz, 1H), 7.61-7.48 (m, 4H), 7.33 (dd, J=5.4, 1.3 Hz, 1H), 5.24 (s, 1H), 4.77-4.40 (m, J=33.2 Hz, 2H), 3.58 (td, J=13.2, 6.6 Hz, 1H), 3.50-3.14 (m, 2H), 2.58 (s, 3H), 1.41 (d, J=6.7 Hz, 6H), 0.95 (s, 9H).

Workup

  1. concentrationmixture concentrated to ˜0.3 mL
  2. additiondiluted with DMF/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-f0406c38f4504f8dbe6d74537637a95e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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