Trifluoroacetic acid → HCID 59011660, compound

HRID 492831Notes

Reaction equation

HRID 492831 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:43])[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O: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:43])[CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O: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][N:24]([C:3]([O:5][C:21]([CH3:26])([CH3:22])[CH3:19])=[O:4])[CH2:23][CH2:22]2)=[O:20])[CH:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86602166HCID 86602166, compound

Product 1

HCID 59011660HCID 59011660, compound

Procedure

t-Butyl 4-{4-[2-fluoro-4-(3-phenylacetylureido)phenoxy]pyridin-2-ylcarbamoyl}piperidine-1-carboxylate (60 mg, 0.101 mmol) and trifluoroacetic acid (0.50 ml) gave a crude product of piperidine-4-carboxylic acid {4-[2-fluoro-4-(3-phenylacetylureido)phenoxy]pyridin-2-yl}amide (ESI-MS (m/z):492). The crude product, formalin (37% aqueous solution; 0.0376 ml, 0.505 mmol), acetic acid (0.0231 ml, 0.404 mmol) and sodium triacetoxyborohydride (42.8 mg, 0.202 mmol) gave the titled compound (51.1 mg, 22.5%) as colorless powder.

Sources & evidence

ORD record
ord-6ff1fd1236184b24a7bb161d272ddf0f
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…