HCID 39247809, compound → HCID 58190611, compound

HRID 1959695Notes

Reaction equation

HRID 1959695 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=O)[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:24][O:25][CH2:26][CH:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1>>[NH:30]1[CH2:29][CH2:28][CH:27]([CH2:26][O:25]/[N:24]=[C:21](/[C:18]2[N:17]=[C:16]3[N:12]([CH2:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[N:13]=[N:14][C:15]3=[N:20][CH:19]=2)\[CH3:22])[CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 39247809HCID 39247809, compound2×HCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 58190611HCID 58190611, compoundYield 15%

Procedure

The title compound was prepared from 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (22.4) and t-butyl 4-(aminooxymethyl)piperidine-1-carboxylate (intermediate J) in 15% yield using the same procedure as described in the synthesis of example 29. 1H-NMR (400 MHz, CDCl3), δ ppm 9.43 (s, 1H), 8.93 (m, 1H), 8.13 (m, 2H), 7.92 (s, 1H), 7.83 (dd, 1H), 7.43 (dd, 1H), 6.10 (s, 2H), 4.20 (d, 2H), 3.18 (d, 2H), 2.68 (t, 2H), 2.37 (s, 3H), 1.98 (br s, 1H), 1.80 (d, 2H), 1.37 (q, 2H). LCMS (method A): [MH]+=417, tR=1.66 min.

Workup

  1. customas described in the synthesis of example 29

Sources & evidence

ORD record
ord-cdb53025428a49cfa184be3ec20953b2
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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