Hydrochloric Acid → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-2-[(2-methyl-4-morpholinyl)methyl]-1,3-thiazole-4-carboxamide

HRID 244760Notes

Reaction equation

Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3S(C2C=CC=CC=2)(=O)=O)=[O:9])[N:7]=1.[CH3:38][CH:39]1[O:44][CH2:43][CH2:42][NH:41][CH2:40]1.[OH-].[Na+].Cl>C(O)(C)C>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:6]4[N:7]=[C:3]([CH2:2][N:41]5[CH2:42][CH2:43][O:44][CH:39]([CH3:38])[CH2:40]5)[S:4][CH:5]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-(Chloromethyl)-N-[6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.091 mmol) and 2-methylmorpholine (0.5 mL, 0.091 mmol) were put in a 0.5-2 mL vial then heated in the microwave at 90° C. for 15 min. The solvent was blown down under nitrogen. Isopropanol (2 mL) and 2M NaOH (2.000 mL) were added and the reaction mixture was stirred for 3 hr at 25° C., then neutralised with 2M HCl aqueous solution until pH=7 (checking with pH paper). The solvent was removed under nitrogen. The mixture was dissolved in 2 mL of DMSO and passed through a hydrophobic frit. Purification was carried out by MDAP to afford the title compound (10 mg).

Workup

customThe solvent was removed under nitrogen
dissolutionThe mixture was dissolved in 2 mL of DMSO
customPurification

Sources & evidence

ORD record: ord-ba4af51304884614961eb57d7df1b950
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658635B2

Reaction notes

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