Triethylamine → 4-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid

HRID 448930Notes

Reaction equation

HRID 448930 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:20]=[C:19]([Cl:21])[C:18]([C:22]2[CH:23]=[N:24][C:25]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:27]=2[C:28]#[N:29])=[CH:17][C:13]=1[C:14]([OH:16])=O)=[O:7])(C)(C)C.[CH3:34][O:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[NH:38][CH3:39].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>ClCCl.CN(C=O)C>[Cl:21][C:19]1[C:18]([C:22]2[CH:23]=[N:24][C:25]([C:30]([F:32])([F:31])[F:33])=[CH:26][C:27]=2[C:28]#[N:29])=[CH:17][C:13]([C:14](=[O:16])[N:38]([C:37]2[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=2[O:35][CH3:34])[CH3:39])=[C:12]([CH:20]=1)[O:11][CH2:10][CH2:9][CH2:8][C:6]([OH:5])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686028022-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid

Product 1

HCID 251589894-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid (30 mg, 0.06 mmol), 2-methoxy-N-methylaniline (9.4 mg, 0.07 mmol), triethylamine (12.5 mg, 0.12 mmol) and 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 35 mg, 0.09 mL) in dichloromethane (1 mL) containing DMF (0.1 mL) was stirred at rt for 16 hrs. The mixture was then partitioned in water and dichloromethane. The organic layer was washed with water, dried and concentrated to yield a crude 4-{5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid t-butyl ester.

Workup

  1. customThe mixture was then partitioned in water
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b3ae6592920410b94269643d05493af
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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