Trifluoroacetic acid → HCID 58727170, compound

HRID 502568Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)[C:15](=[O:29])[CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[N:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)=[CH:35][CH:36]=2)[C:15](=[O:29])[CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)=[N:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 2-(2-((3-(benzo[d]isothiazol-3-ylamino)propyl)((4′-methoxybiphenyl-4-yl)methyl)amino)-2-oxoethyl)pyrrolidine-1-carboxylate (20 mg, 0.033 mmol) was dissolved in methylene chloride (0.5 mL) and cooled in an ice-bath. A cooled solution of trifluoroacetic acid (1.0 mL) in methylene chloride (1.0 mL) was added to the mixture, dropwise. The reaction was allowed to stir for 3 h at 0° C. The solution was concentrated under reduced pressure to yield N-(3-(benzo[d]isothiazol-3-ylamino)propyl)-N-((4′-methoxybiphenyl-4-yl)methyl)-2-(pyrrolidin-2-yl) acetamide (22 mg) as a solid. 1H NMR (300 MHz, CDCl3): 8.15-8.20 (m, 1H), 7.45-7.70 (m, 6H), 7.15-7.20 (m, 2H), 6.90-6.95 (m, 2H), 4.60-4.75 (m, 1H), 4.45-4.55 (m, 1H), 3.95-4.10 (m, 2H), 3.85 (s, 3H), 3.60-3.75 (m, 2H), 3.35-3.45 (m,2H), 3.15-3.25 (m, 2H), 2.75-2.85 (m,1H), 1.90-2.00 ppm (m, 1H). MW=515 confirmed by LC-MS, tr=4.50 min (Method B) MH+=514-516.

Workup

temperaturecooled in an ice-bath
concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-be36b18712b5492cacff996c92febe17
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776847B2

Reaction notes

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