Dimethylformamide → HCID 68558287, compound

HRID 1868491Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C1(C(C2C=CC=CC=2)C(O)=[O:19])C=CC=CC=1.CN(C(ON1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[N:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:52]([CH:54]=O)C.[CH3:56][CH2:57][N:58]([CH:62]([CH3:64])[CH3:63])[CH:59]([CH3:61])C.[F:65][C:66]([F:71])([F:70])[C:67]([O-])=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:52]2[CH2:64][CH:62]([N:58]3[CH2:57][CH2:56][N:41]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:67]=4[C:66]([F:71])([F:70])[F:65])[CH2:61][CH2:59]3)[CH:63]([OH:19])[CH2:54]2)=[O:8])=[CH:9][CH:10]=1

Participants

Reactant 6

HCID 6228Dimethylformamide2×

HCID 63184-Chlorobenzoic Acid

HCID 8333Diphenylacetic Acid

HCID 81531Diisopropylethylamine

HCID 84468Trifluoroacetate

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68558287HCID 68558287, compound

Procedure

The title compound is prepared essentially as described in Example 39 using a mixture of (3R,4R; 3S,4S)-4-[4-(2-trifluoromethyl-phenyl)-piperazin-1-yl]-pyrrolidin-3-ol bistrifluoroacetate (27 mg, 0.05 mmol) and 4-chloro-benzoic acid (7.8 mg, 0.05 mmol), instead of diphenyl acetic acid, preactivated by addition of a solution of HATU in DMF (0.1 mL, 0.05 mmol, 0.5 M), followed by the addition of a solution of DIPEA in DMF (0.1 mL, 0.05 mmol, 1.5 M), to yield 0.9 mg of the title compound as the trifluoroacetate salt. ESIMS ([M+H]+): 454.1 (100).

Workup

customThe title compound is prepared essentially

Sources & evidence

ORD record: ord-6f2c73c31e694bebb98c21553e4fa118
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635698B2

Reaction notes

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