Triethylamine → HCID 86640988, compound

HRID 1972172Notes

Reaction equation

HRID 1972172 reaction equation
[Br:1][C:2]1[C:3]([O:12][C:13]2[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Br[CH2:21][C:22]([CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)=O.C(OC(N1CCC(C(O)=O)CC1)=O)(C)(C)C.C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[C:3]([O:12][C:13]2[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:21]=[C:22]([CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)[N:11]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylateHCID 86640987HCID 86640987, compound

Product 1

HCID 86640988HCID 86640988, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-(5-Bromo-4-(2-methylpyridin-3-yloxy)pyridin-2-yl)thiourea (1.48 g, 4.4 mmol), tert-butyl 4-(2-bromoacetyl)piperidine-1-carboxylate (1.41 g, 4.60 mmol, prepared from 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid utilizing the procedure from Example 1, steps A-C), and triethylamine (0.93 mL, 6.56 mmol) were diluted in ethanol (130 mL). The reaction was stirred at 70° C. overnight and then concentrated. Water was added and the solution was extracted with ethyl acetate, dried and concentrated to give the title compound (2.37 g, 94% yield) as light yellow solid.

Workup

  1. concentrationconcentrated
  2. additionWater was added
  3. extractionthe solution was extracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d217b59498ac4072905e555dea0b5de5
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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