HCID 58532583, compound → HCID 53241449, compound

HRID 2069020Notes

Reaction equation

HRID 2069020 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:45])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:44])[C@@H:33]([N:35](C)[C:36](=O)OC(C)(C)C)[CH3:34])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:46]2[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:45])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:44])[C@@H:33]([NH:35][CH3:36])[CH3:34])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:46]2[CH:47]=[CH:48][C:49]([CH3:52])=[CH:50][CH:51]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 58532583HCID 58532583, compound

Product 1

HCID 53241449HCID 53241449, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the carbamate (7) (25 mg, 0.04 mmol) in DCM/TFA (1:1 v/v, 2.0 mL) was stirred at RT for 30 min. The reaction mixture was evaporated in vacuo and the resulting residue was subjected to SCX capture and release and then purified by flash column chromatography (SiO2, 4 g, 0-100% EtOAc in MeOH, gradient elution) to afford the title compound (Example 9) as an off-white solid (13 mg, 57%): m/z 606 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 1.20 (3H, d), 1.27 (9H, s), 2.26 (3H, s), 2.39 (3H, s), 3.20 (1H, q), 5.38 (2H, s), 6.35 (1H, s), 7.01 (1H, d), 7.28 (1H, dd), 7.36 (2H, m), 7.44 (2H, m), 7.55-7.63 (3H, overlapping m), 7.93 (1H, m), 8.31 (1H, m), 8.34 (1H, dd), 8.36 (1H, br s), 8.60 (1H, s), 8.80 (1H, s).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. custompurified by flash column chromatography (SiO2, 4 g, 0-100% EtOAc in MeOH, gradient elution)

Sources & evidence

ORD record
ord-9561db60956744db813b5ac182e0d060
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

Loading…