Triethylamine → tert-Butyl 2-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-4-methyl-1,3-thiazole-5-carboxylate

HRID 446621Notes

Reaction equation

HRID 446621 reaction equation
Br[C:2]1[S:3][C:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.Cl.Cl.[C:17]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:44])[O:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][N:34]([C:36](=[O:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])[CH3:35])[CH2:28][CH2:27]1.C(N(CC)CC)C>C(O)CCC>[C:17]1([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24]([O:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][N:34]([CH3:35])[C:36](=[O:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:2]2[S:3][C:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=2)[CH2:28][CH2:27]1)=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13015612tert-Butyl 2-bromo-4-methylthiazole-5-carboxylateHCID 666717251-{2-[(6-Aminohexanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate dihydrochloride

Product 1

HCID 86663486tert-Butyl 2-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-4-methyl-1,3-thiazole-5-carboxylateYield 29%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

tert-Butyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (247 mg, 0.739 mmol), the compound (199 mg, 0.369 mmol) obtained in Example 11c, triethylamine (180 μL) and 4.0 mL of n-butanol were used to give the title compound (70 mg; yield, 29%) as a colorless oily substance according to the same procedure as in Example 104b.

Sources & evidence

ORD record
ord-bad5555039de41669897bffaaba4890e
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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