Sodium Bicarbonate → HCID 178505849, compound

HRID 1956368Notes

Reaction equation

C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[N:5]1)(=O)C.C[O-].[Na+].C(=O)(O)[O-].[Na+]>CO>[F:26][C:23]1[CH:22]=[CH:21][C:20]([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[NH:4][N:5]=3)[CH2:19][CH2:18]2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 20 °C

Procedure

1-Acetyl-3-[4-(4-fluorophenyl)piperazin-1-ylmethyl]-1H-indazole (112 mg, 0.32 mmol) in MeOH (3 mL) was treated with sodium methoxide (50 mg) and stirred for 1 h at 20° C. The mixture was poured into saturated aqueous sodium bicarbonate solution (5 mL) and extracted with CH2 Cl2 (3×5 mL). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by flash chromatography (10→100% EtOAc in hexane) to give the title compound as a white solid (52 mg, 52%); mp 191°-192 ° C. (from CH2Cl2 /hexane); 1H NMR (360 MHz, d6 -DMSO) δ12.85 (bs, 1H, NH), 7.88 (d, J=8.9 Hz, 1H, indazole), 7.49 (d, J=8.9 Hz, 1H, indazole), 7.33 (t, J=8.9 Hz, 1H, indazole), 7.09 (t, J=8.9 Hz, 1H, indazole), 7.00 (m, 2 H, Ph), 6.92 (m, 2H, Ph), 3.89 (s, 2H, Ar--CH2N), 3.06 (m, 4H, piperazine), 2.58 (m, 4H, piperazine); MS (CI+) m/e 311 M+H+); Anal. calcd for C18H19N4F.1/4 H2O: C, 68.66; H, 6.24; N, 17.79. Found: C, 68.75; H, 6.13; N, 17.74.

Workup

extractionextracted with CH2 Cl2 (3×5 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated
customthe residue purified by flash chromatography (10→100% EtOAc in hexane)

Sources & evidence

ORD record: ord-4e93fa0638684ab985ba9b8a0477874e
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780475

Reaction notes

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