Triethylamine → Methyl 4-(1-(5-chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate

HRID 72496Notes

Reaction equation

HRID 72496 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.O.ON1C2C=CC=CC=2N=N1.Cl.[NH2:35][C:36]1([C:39]2[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=2)[CH2:38][CH2:37]1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:12][CH:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH2:14]2)=[C:6]([CH:10]=1)[C:7]([NH:35][C:36]1([C:39]2[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=2)[CH2:38][CH2:37]1)=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 679588615-Chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinic acid

Product 1

HCID 67958155Methyl 4-(1-(5-chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 5-chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinic acid (D103) (30 g, 0.0929 mol), 1-Hydroxybenzotriazole hydrate (14.2 g, 0.0929 mol) 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (26.7 g, 0.1394 mol) in dimethylformamide (230 ml) was stirred 40 min at room temperature. A solution of methyl 4-(1-aminocyclopropyl)benzoate (D7) (21.16 g, 0.0929 mol) and triethylamine (12.94 ml, 0.0929 mol) in dimethylformamide (75 ml) was added and the resulting mixture was stirred 3 hours at room temperature. Water (500 ml) was added and the formed precipitate was filtered off and washed with water. After drying it afford the title compound (D151) (41 g)

Workup

  1. stirringthe resulting mixture was stirred 3 hours at room temperature
  2. filtrationthe formed precipitate was filtered off
  3. washwashed with water
  4. customAfter drying it

Sources & evidence

ORD record
ord-be67b26db4824e70beafe0087624a3a3
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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