tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate → HCID 86696430, compound

HRID 870725Notes

Reaction equation

HRID 870725 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:15][CH2:14][CH2:13][C:12]3=[O:16])=[CH:9][N:10]=2)[N:7]=1.[NH2:17][CH2:18][C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>>[O:16]=[C:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:8]1[N:6]2[N:7]=[C:2]([NH:17][CH2:18][C@@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

3

Reactant 2

HCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 86696429HCID 86696429, compound

Product 1

HCID 86696430HCID 86696430, compoundYield 73%

Procedure

The 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)pyrrolidin-2-one was reacted with (S)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate using the amine displacement conditions described in example 5.6.42, Part A to afford the desired product in 73% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.38-1.46 (m, 10H) 1.71 (br. s., 1H) 1.80-1.91 (m, 2H) 1.95-2.08 (m, 1H) 2.22 (quin, J=7.55 Hz, 2H) 2.50-2.58 (m, 2H) 3.22-3.41 (m, 4H) 3.90 (q, J=6.69 Hz, 2H) 4.16 (br. s., 1H) 6.40 (d, J=9.70 Hz, 1H) 7.44 (s, 1H) 7.54 (d, J=9.70 Hz, 1H); LRMS (ESI) m/401.0 [(M+H)+, calcd for C20H28N6O3 400.0].

Sources & evidence

ORD record
ord-7e4ee221e9f248e39d7099865fffbc2f
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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