Triethylamine → HCID 14676879, compound

HRID 1165585Notes

Reaction equation

HRID 1165585 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]1[C:9]2[N:10]([CH3:17])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[S:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[C:25]([O:29][C:30](ON=C(C1C=CC=CC=1)C#N)=[O:31])([CH3:28])([CH3:27])[CH3:26]>O1CCCC1>[CH3:1][N:2]([CH2:3][CH:4]1[C:9]2[N:10]([CH3:17])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[S:7][CH2:6][CH2:5]1)[C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 14676869HCID 14676869, compound

Product 1

HCID 14676879HCID 14676879, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methylaminomethyl-5-methyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole (3.2 g) in dry tetrahydrofuran (30 ml) is allowed to react with triethylamine and 2-t-butoxycarbonyloxyimino-2-phenylacetonitrile in the same manner as in Example 6(a) to give 4-(N-methyl-N-t-butoxycarbonylaminomethyl)-5-methyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole: Yield 87.0%. Mp. 111.5°-114° C. (decomp.) (b) The above product is treated in the same procedure as in Example 12 to give 4-(N-methyl-N-t-butoxycarbonylaminomethyl)-5-methyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole 1-oxide. Mp. 218°-220.5° C. (decomp.). The product is dissolved in methylene chloride (20 ml) and trifluoroacetic acid (4 ml) is added thereto. The mixture is kept at room temperature for 2 hours and then treated in the usual manner to give the title compound (1.13 g): Yield 89.7%.

Sources & evidence

ORD record
ord-089862cf29734febaa6c023c925774fe
Source dataset
uspto-grants-1990_03
Patent number
US04910318

Reaction notes

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