tert-Butyl Formate → 1-tert-Butyl 3-methyl 4-(5-cyanopyridin-2-yl)piperazine-1,3-dicarboxylate

HRID 874964Notes

Reaction equation

HRID 874964 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[N:10]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14][NH:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1.C(OC(C)(C)C)=O>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:13]2[CH2:14][CH2:15][N:10]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:11][CH:12]2[C:16]([O:18][CH3:19])=[O:17])=[N:3][CH:4]=1)#[N:7]

Participants

4

Reactant 3

HCID 61207tert-Butyl FormateHCID 27568191-tert-Butyl 3-methyl piperazine-1,3-dicarboxylateHCID 50057186-Bromopyridine-3-carbonitrile

Product 1

HCID 709753381-tert-Butyl 3-methyl 4-(5-cyanopyridin-2-yl)piperazine-1,3-dicarboxylateYield 36%

Procedure

This compound was synthesized from 6-bromonicotinonitrile and 1-tert-butyl 3-methyl piperazine-1,3-dicarboxylate as described for example 43 step 1 (200 mg, yield 36%). 1H NMR (400 MHz, CDCl3) δ 8.42 (d, J=2.3 Hz, 1H), 7.72-7.69 (dd, J=9.0 Hz, 2.3 Hz, 1H), 6.68 (d, J=9.0 Hz, 1H), 5.35 (m, 1H), 4.67-4.64 (d, J=13.6 Hz, 1H), 4.19 (m, 1H), 3.81-3.79 (d, J=9.8 Hz, 1H), 3.73 (s, 3H), 3.53-3.48 (m, 1H), 3.27-3.23 (m, 1H), 3.06 (m, 1H), 1.47 (s, 9H). MS (ESI) m/z: Calculated for C17H22N4O4: 346.16. found: 247.2 (M+H-Boc)+

Sources & evidence

ORD record
ord-ffc3255c6e41488f9047bd457ac4b284
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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