Trifluoroacetic acid → 3-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-(methoxycarbonyl)pyridin-2-yl)benzoic acid

HRID 2188967Notes

Reaction equation

HRID 2188967 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13]([C:15]1[CH:16]=[C:17]([C:21]2[N:30]=[C:29]([NH:31][C:32]([C:34]3([C:37]4[CH:47]=[CH:46][C:40]5[O:41][C:42]([F:45])([F:44])[O:43][C:39]=5[CH:38]=4)[CH2:36][CH2:35]3)=[O:33])[CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])[CH:18]=[CH:19][CH:20]=1)=[O:14])(C)(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:45][C:42]1([F:44])[O:41][C:40]2[CH:46]=[CH:47][C:37]([C:34]3([C:32]([NH:31][C:29]4[N:30]=[C:21]([C:17]5[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=5)[C:13]([OH:14])=[O:12])[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=4)=[O:33])[CH2:36][CH2:35]3)=[CH:38][C:39]=2[O:43]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59166109Methyl 2-(3-(tert-butoxycarbonyl)phenyl)-6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)nicotinate

Product 1

HCID 591659443-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-(methoxycarbonyl)pyridin-2-yl)benzoic acidYield 96.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

TFA (1 mL) was added to a solution of methyl 2-(3-(tert-butoxycarbonyl)-phenyl)-6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)nicotinate (290 mg, 0.50 mmol) in CH2Cl2 (2.5 mL). The reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with CH2Cl2 and neutralized with saturated aqueous NaHCO3. A white precipitate formed which was filtered, washed with H2O and air-dried to yield the product as a white solid (240 mg, 91%). ESI-MS m/z calc. 496.1. found 497.5 (M+1)+. Retention time 1.91 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.24 (d, J=8.7 Hz, 1H), 8.11 (d, J=8.7 Hz, 1H), 7.98-7.96 (m, 2H), 7.62 (d, J=7.8 Hz, 1H), 7.55-7.51 (m, 2H), 7.40-7.33 (m, 2H), 3.62 (s, 3H), 1.55-1.52 (m, 2H), 1.22-1.19 (m, 2H).

Workup

  1. customA white precipitate formed which
  2. filtrationwas filtered
  3. washwashed with H2O
  4. customair-dried

Sources & evidence

ORD record
ord-2fdd71d65f5446468329b7532a59c390
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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