2-Amino-2-methyl-1,3-propanediol → HCID 51030561, compound

HRID 1624019Notes

Reaction equation

HRID 1624019 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3]O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:22]3[C@@H:21]4[CH2:23][C@@H:20]4[CH2:19][C:18]=3[C:17]([C:24](O)=[O:25])=[N:16]2)=[N:13][CH:14]=1.[C@@H]12C[C@@H]1CCC2=O.ClC1C=CC(NN)=NC=1>>[OH:6][CH2:5][C:2]([NH:1][C:24]([C:17]1[C:18]2[CH2:19][C@H:20]3[CH2:23][C@H:21]3[C:22]=2[N:15]([C:12]2[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][N:13]=2)[N:16]=1)=[O:25])([CH3:7])[CH3:3]

Participants

5

Reactant 4

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 11615157(1R,5S)-bicyclo[3.1.0]hexan-2-oneHCID 135904645-Chloro-2-hydrazinylpyridineHCID 68182295HCID 68182295, compound

Product 1

HCID 51030561HCID 51030561, compound

Procedure

The title compound was prepared in a manner similar to that described in Method G using 2-amino-2-methylpropane-1,3-diol and (1aR,5aR)-2-(5-Chloropyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid. The aforementioned acid was prepared in a similar method as described in Method A and B using (1R,5S)-bicyclo[3,1,0]hexan-2-one and 5-chloro-2-hydrazinylpyridine. LCMS m/z=347.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.45 (td, J=4.7, 3.3 Hz, 1H), 1.25 (td, J=8.3, 4.4 Hz, 1H), 1.406 (s, 3H), 1.410 (s, 3H), 2.24-2.30 (m, 1H), 2.75-2.80 (m, 1H), 2.90 (d, J=16.6 Hz, 1H), 3.00 (dd, J=16.6, 6.4 Hz, 1H), 3.70 (s, 2H), 4.63 (bs, 1H), 6.92 (s, 1H), 7.78 (dd, J=8.7, 2.5 Hz, 1H), 7.87 (dd, J=8.8, 0.6 Hz, 1H), 8.41 (dd, J=2.5, 0.6 Hz, 1H).

Workup

  1. customThe aforementioned acid was prepared in a similar method

Sources & evidence

ORD record
ord-c42f4677686e44fe8bd1d9bb2c9035e0
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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