tert-butyl N-(prop-2-yn-1-yl)carbamate → HCID 57886023, compound

HRID 1819076Notes

Reaction equation

HRID 1819076 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13](I)=[CH:14][C:6]1=2.[C:21]([NH:28][CH2:29][C:30]#[CH:31])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>>[C:24]([O:23][C:21](=[O:22])[NH:28][CH2:29][C:30]#[C:31][C:13]1[CH:12]=[N:11][C:7]2[NH:8][CH2:9][CH2:10][N:5]([CH2:4][C:3]3[C:2]([Cl:1])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:20])[C:6]=2[CH:14]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 57885814HCID 57885814, compound

Product 1

HCID 57886023HCID 57886023, compound

Procedure

1-(2,6-Dichlorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (1.951 g) was coupled with N-boc propargylamine as in General Procedure 5 to give the title compound as an orange solid. LCMS: m/z=447.53 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.40 (9H, s), 2.86 (2H, m), 3.27 (2H, m), 3.95 (2H, d, J=5.6 Hz), 4.46 (2H, s), 6.86 (1H, s), 6.89 (1H, s), 7.29 (1H, m), 7.42 (2H, m), 7.54 (2H, d, J=8.3 Hz).

Sources & evidence

ORD record
ord-5c9a442f076f4e968b25b0b055eb02f5
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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