HCID 3270682, compound → HCID 10410100, compound

HRID 1349918Notes

Reaction equation

C(O[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=2)[CH:16]=1)=[NH:5])C.[NH2:27][NH:28][C:29](=O)[CH2:30][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C[O-].[Na+]>CO>[CH3:26][O:25][C:20]1[CH:19]=[CH:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([C:9]3[C:13]4[C:12](=[CH:8][CH:7]=[C:6]([C:4]5[N:5]=[C:29]([CH2:30][N:31]6[CH2:35][CH2:34][CH2:33][CH2:32]6)[NH:28][N:27]=5)[CH:14]=4)[NH:11][N:10]=3)[CH:16]=2)[CH:21]=1

Participants

Conditions

Temperature: 95 °C

Procedure

The title compound was prepared using the same procedure as for Example 423. To a suspension of ethoxy[3-(6-methoxy(2-naphthyl))(1H-indazol-5-yl)]methanimine (0.386 g, 1.01 mmol) in methanol (5 mL) was added N-amino-2-pyrrolidinylacetamide (0.433 g, 3.03 mmol) and 4.3 M sodium methoxide (0.518 mL, 2.23 mmol). The mixture was heated in a sealed tube at 95° C. for 16 h. The solvent was removed using a rotary evaporator which gave a solid residue. Purification of the residue by preparative HPLC (30–100%, acetonitrile/water) gave the title compound (0.045 g, 10% yield): 1H NMR (DMSO-d6) δ 13.41 (br s, 1H), 8.73 (s, 1H), 8.44 (s, 1H), 8.09 (t, 2H), 8.00 (t, 2H), 7.68 (d, 1H), 7.39 (d, 1H), 7.23 (dd, 1H), 3.91 (s, 3H), 3.75 (s, 2H), 2.53 (m, 4H), 2.49 (m, 4H); ES-MS (m/z) 425 [M+1]+.

Workup

customThe title compound was prepared
customThe solvent was removed
customa rotary evaporator which
customgave a solid residue
customPurification of the residue by preparative HPLC (30–100%, acetonitrile/water)

Sources & evidence

ORD record: ord-fa5b1d94408945dab76ea0d2d2127b84
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211594B2

Reaction notes

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