(Rac)-{1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester → (Rac)-{1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrrolidin-3-yl}-methylamine

HRID 69269Notes

Reaction equation

HRID 69269 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH2:23][C:24]4[CH:25]=[C:26]5[C:31](=[CH:32][C:33]=4[F:34])[N:30]=[CH:29][CH:28]=[CH:27]5)=[CH:21][N:22]=3)[N:19]=2)[CH2:10]1)C)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:34][C:33]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][CH:29]=[N:30]2)=[CH:25][C:24]=1[CH2:23][C:20]1[N:18]2[N:19]=[C:14]([N:11]3[CH2:12][CH2:13][CH:9]([NH:7][CH3:6])[CH2:10]3)[CH:15]=[CH:16][C:17]2=[N:22][CH:21]=1

Participants

4

Reactant 1

HCID 68630829(Rac)-{1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester

Product 1

HCID 57917262(Rac)-{1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrrolidin-3-yl}-methylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(rac)-{1-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester (Stage 260.1, 179 mg, 0.376 mmol) was dissolved in DCM (7.5 mL) and TFA (3 mL). The RM was stirred at rt for 1 h. A basic work up (1 M Na2CO3) followed by a crystallization in Et2O afforded the title compound as white crystals (tR 2.28 min (conditions 13), MH+=377, 1H-NMR in DMSO-d6: 8.83 (m, 1H); 8.30 (d, 1H); 7.93 (d, 1H); 7.75 (m, 2H); 7.48 (dd, 1H); 7.35 (s, 1H); 6.74 (d, 1H); 4.37 (s, 2H); 3.52-3.35 (m, 3H); 3.23-3.17 (m, 2H); 2.27 (s, 3H); 2.07 (m, 1H); 1.86 (bs, 1H); 1.80 (m, 1H)).

Workup

  1. customA basic work up (1 M Na2CO3) followed by a crystallization in Et2O

Sources & evidence

ORD record
ord-392ade4551044cd8bf9a8a658e925891
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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