Triethylamine → t-butyl 3-amino-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]indene-2-carboxylate

HRID 1991452Notes

Reaction equation

HRID 1991452 reaction equation
[SH:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[C:4]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:3]=1[C:18]#[N:19].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)CC)C.C[O-].[Na+]>C(O)C>[NH2:19][C:18]1[C:3]2[C:4]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[C:5]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]3=[N:7][C:2]=2[S:1][C:21]=1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 10942334Sodium MethoxideHCID 1785105404-(2-Thienyl)-2-thioxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[B]pyridine-3-carbonitrile

Product 1

HCID 11625499t-butyl 3-amino-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]indene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-mercapto-4-thien-2-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile (143 mg, 0.5 mmol), tert-butyl bromoacetate (97 mg, 0.5 mmol) and triethyl amine (51 mg, 0.5 mmol) in ethanol (20 mL) was stirred at room temperature overnight, followed by the addition of NaOMe (30 mg, 0.56 mmol). The mixture was then refluxed for 30 min., and poured onto ice. The precipitate is filtered and washed with water to furnish pure t-butyl 3-amino-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]indene-2-carboxylate.

Workup

  1. temperatureThe mixture was then refluxed for 30 min.
  2. additionpoured onto ice
  3. filtrationThe precipitate is filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-00666a41b37c4ce1b80c1892ff44a25b
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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