2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde → 4-(2-{(2S,5R)-5-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-2-yl}ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

HRID 255373Notes

Reaction equation

HRID 255373 reaction equation
[NH2:1][C@@H:2]1[CH2:7][N:6](C(OC(C)(C)C)=O)[C@@H:5]([CH2:15][CH2:16][N:17]2[C:22]3[CH:23]=[C:24]([C:27]#[N:28])[CH:25]=[CH:26][C:21]=3[O:20][CH2:19][C:18]2=[O:29])[CH2:4][CH2:3]1.N[C@H]1CN(C(OC(C)(C)C)=O)[C@H](CCN2C3C=C(C#N)C=CC=3OCC2=O)CC1.[Si](O[C@@H]1CN(C(OC(C)(C)C)=O)[C@H](C(OCC)=O)CC1)(C(C)(C)C)(C)C.[Si](O[C@H]1CN(C(OC(C)(C)C)=O)[C@@H](C(OCC)=O)CC1)(C(C)(C)C)(C)C.[O:111]1[C:120]2[CH:119]=[C:118]([CH:121]=O)[N:117]=[CH:116][C:115]=2[O:114][CH2:113][CH2:112]1>>[O:111]1[C:120]2[CH:119]=[C:118]([CH2:121][NH:1][C@H:2]3[CH2:7][NH:6][C@H:5]([CH2:15][CH2:16][N:17]4[C:22]5[CH:23]=[C:24]([C:27]#[N:28])[CH:25]=[CH:26][C:21]=5[O:20][CH2:19][C:18]4=[O:29])[CH2:4][CH2:3]3)[N:117]=[CH:116][C:115]=2[O:114][CH2:113][CH2:112]1

Participants

6

Reactant 5

HCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 66774232tert-Butyl (2R,5S)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylateHCID 66775001tert-butyl (2S,5R)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylateHCID 691850781-tert-butyl 2-ethyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylateHCID 866426621-tert-butyl 2-ethyl (2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylate

Product 1

HCID 667748244-(2-{(2S,5R)-5-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-2-yl}ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

Procedure

The product was obtained following the procedure described for Example 105, except, the enantiomer of Intermediate 183, tert-butyl (2S,5R)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate (prepared by the exact route as Intermediate 183, but starting from 1-tert-butyl 2-ethyl (2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylate, the enantiomer of Intermediate 191) was reacted with 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde to yield the named compound.

Workup

  1. customThe product was obtained
  2. customto yield the named compound

Sources & evidence

ORD record
ord-e0e3ac3eaf3f44cab19d4568b58ae558
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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