Sodium hydride → HCID 68183227, compound

HRID 513771Notes

Reaction equation

HRID 513771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[N:15]3)[NH:12][S:11](=[O:21])(=[O:20])[C:10]1[C:5]2=[CH:6][C:7](F)=[CH:8][CH:9]=1.C([N:30]1[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31]1)(OC(C)(C)C)=O.[H-].[Na+]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[N:15]3)[NH:12][S:11](=[O:21])(=[O:20])[C:10]1[C:5]2=[CH:6][C:7]([O:35][CH:32]2[CH2:33][CH2:34][NH:30][CH2:31]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 44169391-Boc-3-pyrrolidinolHCID 6818318212-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 68183227HCID 68183227, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a similar fashion using route 51 general procedure 119, 12-chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 503 (0.2 g, 0.6 mmol), 1-boc-3-pyrrolidinol (0.45 g, 2.3 mmol), NaH (60% in mineral oil; 57 mg, 2.3 mmol) and NMP (2 ml) gave the title compound (33 mg, 14%) after purification by preparative HPLC (acidic conditions 2). Boc deprotection occurred in situ during heating.

Sources & evidence

ORD record
ord-e59a37493a3649a79affcb58196a3cc0
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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