Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-{[(1aS,5aS)-2-(4-Chloro-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl]-amino}-3-fluoro-3-methyl-butyric Acid Methyl Ester

HRID 1624006Notes

Reaction equation

CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([N:32]2[C:39]3[C@H:38]4[CH2:40][C@H:37]4[CH2:36][C:35]=3[C:34]([C:41]([OH:43])=O)=[N:33]2)[CH:27]=1.Cl.[NH2:45][CH:46]([C:51]([F:54])([CH3:53])[CH3:52])[C:47]([O:49][CH3:50])=[O:48]>>[CH3:50][O:49][C:47](=[O:48])[CH:46]([NH:45][C:41]([C:34]1[C:35]2[CH2:36][C@@H:37]3[CH2:40][C@@H:38]3[C:39]=2[N:32]([C:28]2[CH:27]=[C:26]([Cl:25])[CH:31]=[CH:30][N:29]=2)[N:33]=1)=[O:43])[C:51]([F:54])([CH3:53])[CH3:52]

Participants

Reactant 3

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

HCID 68182488HCID 68182488, compound

HCID 866697111268883-34-6

Product 1

HCID 681823882-{[(1aS,5aS)-2-(4-Chloro-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl]-amino}-3-fluoro-3-methyl-butyric Acid Methyl Ester

Procedure

The title compound was prepared by HATU coupling method using (1aS,5aS)-2-(4-chloro-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid and methyl 2-amino-3-fluoro-3-methylbutanoate hydrochloride. LCMS m/z=407.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 0.42-0.50 (m, 1H), 1.23-1.30 (m, 1H), 1.49 (d, J=21.6 Hz, 3H), 1.57 (d, J=21.0 Hz, 3H), 2.22-2.30 (m, 1H), 2.79-2.85 (m, 1H), 2.87-3.05 (m, 2H), 3.81 (s, 3H), 4.85-4.94 (m, 1H), 7.22 (dd, J=5.4 and 1.8 Hz, 1H), 7.56 (d, J=9.5 Hz, 1H), 8.01 (d, J=1.8 Hz, 1H), 8.35 (d, J=5.4 Hz, 1H).

Sources & evidence

ORD record: ord-fe49bdfa120747279c3d8a8e39a2a8dc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778950B2

Reaction notes

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