HCID 58532540, compound → HCID 53241790, compound

HRID 2069019Notes

Reaction equation

HRID 2069019 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:46])[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:45])[C:33]([N:36](C)[C:37](=O)OC(C)(C)C)([CH3:35])[CH3:34])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:47]2[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=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:46])[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:45])[C:33]([CH3:35])([NH:36][CH3:37])[CH3:34])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:47]2[CH:48]=[CH:49][C:50]([CH3:53])=[CH:51][CH:52]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 58532540HCID 58532540, compound

Product 1

HCID 53241790HCID 53241790, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the carbamate (6) (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 to afford the title compound (Example 8) as a pale brown solid (20 mg, 89%): m/z 620 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 1.25 (6H, s), 1.27 (9H, s), 2.20 (3H, s), 2.39 (3H, s), 5.38 (2H, s), 6.35 (1H, s), 7.00 (1H, d), 7.27 (1H, dd), 7.36 (2H, m), 7.44 (2H, m), 7.58-7.62 (3H, overlapping m), 7.93 (1H, m), 8.29-8.34 (3H, overlapping m), 8.59 (1H, br s), 8.79 (1H, br s).

Workup

  1. customThe reaction mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-955315e5162043d29d861b864db3dc4a
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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