tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate → HCID 57899016, compound

HRID 911080Notes

Reaction equation

HRID 911080 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13]3[N:18]=[CH:17][C:16]([S:19][CH2:20][CH2:21]C(OC)=O)=[C:15]([O:26][C:27]4[CH:36]=[CH:35][CH:34]=[C:33]5[C:28]=4[CH:29]=[CH:30][CH:31]=[N:32]5)[CH:14]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].BrCC1[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]1>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13]3[N:18]=[CH:17][C:16]([S:19][CH2:20][CH:21]4[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52])[CH2:47][CH2:46]4)=[C:15]([O:26][C:27]4[CH:36]=[CH:35][CH:34]=[C:33]5[C:28]=4[CH:29]=[CH:30][CH:31]=[N:32]5)[CH:14]=3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 86634788HCID 86634788, compound

Product 1

HCID 57899016HCID 57899016, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure of Example 201, methyl 3-(6-(4-phenylthiazol-2-ylamino)-4-(quinolin-5-yloxy)pyridin-3-ylthio)propanoate (0.200 g, 0.389 mmol) (prepared as in Example 137), THF (10 mL), potassium 2-methylpropan-2-olate (1.36 ml, 1.36 mmol), tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (0.108 g, 0.389 mmol) were combined to give tert-butyl 4-((6-(4-phenylthiazol-2-ylamino)-4-(quinolin-5-yloxy)pyridin-3-ylthio)methyl)piperidine-1-carboxylate (0.15 g, 61% yield) as yellow solid. 1H NMR (CDCl3) δ 8.94 (dd, 1H), 8.36 (s, 1H), 8.17 (d, 1H), 7.98 (dd, 1H), 7.55 (t, 1H), 7.49 (s, H), 7.47 (s, 1H), 7.35 (dd, 1H), 7.12 (m, 3H), 6.94 (d, 1H), 6.84 (s, 1H), 6.02 (s, 1H), 2.18 (d, 2H), 2.61 (t, 2H), 1.81 (m, 2H), 1.60 (m, 1H), 1.40 (s, 9H), 1.22 (t, 2H), 1.12 (m, 2H).

Sources & evidence

ORD record
ord-36503e1e7bd7448994353423af037647
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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