Isopropanol → 2-(4-Morpholinylmethyl)-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 244759Notes

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:25]=[CH:24][N:23]=[C:22]4[N:26](S(C5C=CC=CC=5)(=O)=O)[CH:27]=[CH:28][C:21]=34)[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.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(O)(C)C.[OH-].[Na+]>CS(C)=O>[N:47]1([CH2:2][C:3]2[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][N:23]=[C:22]5[NH:26][CH:27]=[CH:28][C:21]=45)[CH:17]=[C:16]4[C:12]=3[CH:13]=[N:14][NH:15]4)=[O:9])[N:7]=2)[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-(Chloromethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide (30 mg, 0.044 mmol) and morpholine (0.5 ml, 5.74 mmol) were mixed then heated in the microwave for 15 min at 90° C. The solvent was blown off under nitrogen. Isopropanol (1.5 mL) and 2M NaOH (1.500 ml) were added. The reaction mixture was stirred for 1.5 h. Further Isopropanol (1.5 mL) and 2M NaOH (1.5 mL) were added to the mixture which was stirred for 26 hours. The solvent was blown off under nitrogen. The resultant solid was dissolved in DMSO (2 mL). The salts were removed by filtration and the mixture was purified by MDAP to afford the title compound (4 mg).

Workup

stirringwas stirred for 26 hours
customThe salts were removed by filtration
customthe mixture was purified by MDAP

Sources & evidence

ORD record: ord-bd908900a59e4f678a378e1e26b9ba44
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658635B2

Reaction notes

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