Cesium carbonate → (6R)-9-fluoro-17-methyl-13-oxa-2,11,17,21,22,25-hexazapentacyclo[17.5.2.02,6.07,12.022,26]hexacosa-1(25),7(12),8,10,19(26),20,23-heptaen-18-one

HRID 1426934Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]([CH3:30])[C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@@H:18]3[C:22]3[C:23](=[O:29])[NH:24][CH:25]=[C:26]([F:28])[CH:27]=3)=[N:13][C:12]=12)=[O:7].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:28][C:26]1[CH:27]=[C:22]2[C:23](=[N:24][CH:25]=1)[O:29][CH2:2][CH2:3][CH2:4][N:5]([CH3:30])[C:6](=[O:7])[C:8]1=[C:12]3[N:13]=[C:14]([CH:15]=[CH:16][N:11]3[N:10]=[CH:9]1)[N:17]1[C@@H:18]2[CH2:19][CH2:20][CH2:21]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (R)-N-(3-chloropropyl)-5-(2-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)-N-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide (50 mg, 0.12 mmol) and Cs2CO3 (188 mg, 0.58 mmol) in DMF (12 mL) was heated at 90° C. for 15 minutes to reach completion. The reaction mixture was filtered, rinsed with DMF, and concentrated. The crude material was purified directly by reverse-phase column chromatography, eluting with 5 to 60% acetonitrile/water to yield the title product as pale yellow powder (17 mg, 36% yield). MS (apci) m/z=397.3 (M+H).

Workup

filtrationThe reaction mixture was filtered
washrinsed with DMF
concentrationconcentrated
customThe crude material was purified directly by reverse-phase column chromatography
washeluting with 5 to 60% acetonitrile/water

Sources & evidence

ORD record: ord-b7e859b18fe648fdbf54003b7f94116d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933084B2

Reaction notes

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