Trifluoroacetic acid → t-Butyl 4-(4-{2-fluoro-4-[3-(4-fluorophenyl)acetylthioureido]phenoxy}pyridin-2-ylcarbamoyl)piperidine-1-carboxylate

HRID 492830Notes

Reaction equation

HRID 492830 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[F:8][C:9]1[CH:30]=[C:29]([NH:31][C:32]([NH:34][C:35](=[O:44])[CH2:36][C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)=[S:33])[CH:28]=[CH:27][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])[CH:13]=1>>[F:8][C:9]1[CH:30]=[C:29]([NH:31][C:32]([NH:34][C:35](=[O:44])[CH2:36][C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)=[S:33])[CH:28]=[CH:27][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]([CH:21]2[CH2:22][CH2:23][N:24]([C:3]([O:5][C:21]([CH3:26])([CH3:22])[CH3:19])=[O:4])[CH2:25][CH2:26]2)=[O:20])[CH:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86602165Piperidine-4-carboxylic acid (4-{2-fluoro-4-[3-(4-fluorophenyl)acetylthioureido]phenoxy}pyridin-2-yl}amide

Product 1

HCID 23153119t-Butyl 4-(4-{2-fluoro-4-[3-(4-fluorophenyl)acetylthioureido]phenoxy}pyridin-2-ylcarbamoyl)piperidine-1-carboxylate

Procedure

t-Butyl 4-(4-{2-fluoro-4-[3-(4-fluorophenyl)acetylthioureido]phenoxy}pyridin-2-ylcarbamoyl)piperidine-1-carboxylate (38.8 mg, 0.062 mmol) and trifluoroacetic acid (0.50 ml) gave a crude product of piperidine-4-carboxylic acid (4-{2-fluoro-4-[3-(4-fluorophenyl)acetylthioureido]phenoxy}pyridin-2-yl}amide (ESI-MS (m/z):526). The crude product, formalin (37% aqueous solution; 0.0231 ml), acetic acid (0.0142 ml) and sodium triacetoxyborohydride (26.3 mg) gave the titled compound (1.1 mg, 3.29%) as colorless powder.

Sources & evidence

ORD record
ord-76ca774022e140d28320771b1e7adb8d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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