4-(1-Pyrrolidinyl)piperidine → HCID 57580529, compound

HRID 1692423Notes

Reaction equation

HRID 1692423 reaction equation
[CH:1]1([C:4]2[C:9]([C:10]([OH:12])=O)=[C:8]([CH3:13])[N:7]=[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16](C(F)(F)F)[CH:15]=3)[N:5]=2)[CH2:3][CH2:2]1.Cl.[F:25][C:26]([F:38])([F:37])[O:27]C1C=C(C=CC=1)C(N)=N.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:63]1([CH:68]2[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]2)[CH2:67][CH2:66][CH2:65][CH2:64]1>CN(C=O)C.C(N(CC)CC)C>[CH:1]1([C:4]2[C:9]([C:10]([N:71]3[CH2:72][CH2:73][CH:68]([N:63]4[CH2:67][CH2:66][CH2:65][CH2:64]4)[CH2:69][CH2:70]3)=[O:12])=[C:8]([CH3:13])[N:7]=[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:27][C:26]([F:38])([F:37])[F:25])[CH:15]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225635033-(Trifluoromethoxy)benzene-1-carboximidamide--hydrogen chloride (1/1)HCID 66901575HCID 66901575, compound2×

Product 1

HCID 57580529HCID 57580529, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

In analogy to the procedure described for intermediate 2,4-cyclopropyl-6-methyl-2-(3-trifluoromethoxy-phenyl)-pyrimidine-5-carboxylic acid [prepared in analogy to the preparation of 4-cyclopropyl-6-methyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (intermediate 7), by using 3-trifluoromethoxy-benzamidine hydrochloride instead of 3-trifluoromethyl-benzamidine hydrochloride in the reaction step analogous to the preparation of intermediate 7A] was reacted with HATU, triethylamine and 4-pyrrolidin-1-yl-piperidine in DMF. Subsequent purification by preparative HPLC afforded the title compound as a gum. MS: 475.3 (MH+).

Workup

  1. customin the reaction step
  2. customSubsequent purification by preparative HPLC

Sources & evidence

ORD record
ord-405acaa60ed1430fadb7e483d450006a
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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