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

HRID 1848642Notes

Reaction equation

HRID 1848642 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-9321c97a96d247acb49823ca36f27f7a
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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