Chlorosuccinimide → HCID 24968571, compound

HRID 1660905Notes

Reaction equation

HRID 1660905 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:17](=[O:19])[N:16]([CH2:20][C@@H:21]([OH:24])[CH2:22][OH:23])[CH:15]=[N:14][C:13]=3[N:12]([CH3:25])[C:11](=[O:26])[CH:10]=2)=[C:4]([F:27])[CH:3]=1.C1C(=O)N([Cl:35])C(=O)C1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:17](=[O:19])[N:16]([CH2:20][C@@H:21]([OH:24])[CH2:22][OH:23])[CH:15]=[N:14][C:13]=3[N:12]([CH3:25])[C:11](=[O:26])[C:10]=2[Cl:35])=[C:4]([F:27])[CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58191933HCID 58191933, compound

Product 1

HCID 24968571HCID 24968571, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 20C (60 mg, 0.136 mmol) was dissolved in 2 mL DCM. NCS (22 mg, 0.165 mmol) was added. The mixture was stirred at room temperature overnight. Example 29 (35.3 mg, 54%) was isolated by preparative HPLC separation. 1H NMR (400 MHz, MeOD) δ 8.50 (s, 1H) 7.45 (d, J=8.0 Hz, 1H) 7.38 (d, J=8.0 Hz, 1H) 7.10 (t, J=8.0 Hz, 1H) 4.51 (m, 1H) 4.03 (m, 1H) 3.88 (m, 1H), 3.82 (s, 3H) 3.68 (d, J=4 Hz, 2H). [M+H] calc'd for C17H15BrClFN4O4, 475; found, 475.

Sources & evidence

ORD record
ord-65a3586c326a49e9b2cf22884a3002d5
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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