Propargyl chloroformate → prop-2-ynyl 4-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]-1-piperidyl]-4-methyl-piperidine-1-carboxylate

HRID 1642501Notes

Reaction equation

HRID 1642501 reaction equation
[CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C@H:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:25]([O:27][CH2:28][C:29]#[CH:30])=[O:26]>>[O:23]=[C:15]1[N:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:2]3([CH3:1])[CH2:7][CH2:6][N:5]([C:25]([O:27][CH2:28][C:29]#[CH:30])=[O:26])[CH2:4][CH2:3]3)[CH2:9][CH2:10]2)[C@H:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]2[NH:16]1

Participants

3

Reactant 2

HCID 3356829Propargyl chloroformateHCID 57619802(3aS,7aS)-1-[1-(4-methyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one

Product 1

HCID 25221448prop-2-ynyl 4-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]-1-piperidyl]-4-methyl-piperidine-1-carboxylateYield 9.5%

Procedure

Following the procedure used in example 16 and starting from (3aS,7aS)-3-[1-(4-methyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-one (HCl salt, 181 mg, 0.51 mmol) and prop-2-ynyl chloroformate (0.050 mL, 0.51 mmol), the title compound (19.40 mg, 9.50%) was obtained after purification by preparative LC/MS (high pH). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.29-1.47 (m, 5H), 1.49 (s, 3H), 1.76-2.01 (m, 8H), 2.29-2.44 (m, 2H), 2.82 (t, J=9.96 Hz, 5H), 2.90 (d, J=10.55 Hz, 2H), 3.03 (d, J=6.64 Hz, 1H), 3.68 (t, J=9.57 Hz, 2H), 4.06-4.17 (m, 1H), 4.27 (d, J=19.53 Hz, 2H), 4.52 (s, 1H), 4.69 (s, 1H), 4.76 (s, 1H). MS (M+1): 403.3.

Sources & evidence

ORD record
ord-7bbfdd9030b44f6580f0bce9a29d2f00
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

Loading…