Cesium carbonate → HCID 58382296, compound

HRID 1628028Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[N:24]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:15]3=[N:16][CH:17]=[C:18]4[CH:22]=[N:21][N:20]([CH3:23])[C:19]4=[C:14]3[CH:13]=2)=[CH:3]1.Cl[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:36][CH2:37][N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[CH:8][CH:9]=2)[C:4]([C:12]2[N:24]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:15]3=[N:16][CH:17]=[C:18]4[CH:22]=[N:21][N:20]([CH3:23])[C:19]4=[C:14]3[CH:13]=2)=[CH:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-methyl-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-ol (0.21 g, 0.42 mmol), 4-(2-chloroethyl)morpholine (0.12 g, 0.78 mmol, Beta Pharm) and Cs2CO3 (0.42 g, 1.27 mmol) in DMF (4 mL) was heated at about 50° C. for about 20 h. After cooling to rt the mixture was filtered. The filtrate was purified by preparative reverse phase HPLC (Table 2, Method j) to give 4-(2-(1-methyl-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-yloxy)ethyl)morpholine (0.053 g, 21%): LC/MS (Table 2, Method a) Rt=2.07 min; MS m/z 585 (M+H)+.

Workup

temperatureAfter cooling to rt the mixture
filtrationwas filtered
customThe filtrate was purified by preparative reverse phase HPLC (Table 2, Method j)

Sources & evidence

ORD record: ord-34facdd4fabb49358bcc799868848e18
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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