Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride → Methyl 4-(1-(2-(3-((5-fluoropyrimidin-2-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoate

HRID 72524Notes

Reaction equation

HRID 72524 reaction equation
ClC1C=NC(N2CC(NC3C=CC(F)=CC=3F)C2)=C(C=1)C([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=O.[F:37][C:38]1[CH:39]=[N:40][C:41]([O:44][CH:45]2[CH2:48][N:47]([C:49]3[N:57]=[CH:56][C:55]([C:58]([F:61])([F:60])[F:59])=[CH:54][C:50]=3[C:51]([OH:53])=O)[CH2:46]2)=[N:42][CH:43]=1.Cl.NC1(C2C=CC(C(OC)=O)=CC=2)CC1>>[F:37][C:38]1[CH:43]=[N:42][C:41]([O:44][CH:45]2[CH2:48][N:47]([C:49]3[N:57]=[CH:56][C:55]([C:58]([F:61])([F:60])[F:59])=[CH:54][C:50]=3[C:51]([NH:9][C:10]3([C:13]4[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=4)[CH2:12][CH2:11]3)=[O:53])[CH2:46]2)=[N:40][CH:39]=1

Participants

4

Reactant 3

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 67958748HCID 67958748, compoundHCID 679588812-(3-((5-Fluoropyrimidin-2-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid

Product 1

HCID 67958127Methyl 4-(1-(2-(3-((5-fluoropyrimidin-2-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoate

Procedure

The title compound (D182) (36 mg) was prepared according to the experimental procedure described in Description (D169) starting from 2-(3-((5-fluoropyrimidin-2-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid (D131) (42 mg, 0.117 mmol) and methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (27 mg, 0.117 mmol).

Sources & evidence

ORD record
ord-6dd91fbf0bcd473a97384028a2e713ba
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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