Dimethyl N-cyanodithioiminocarbonate → HCID 178503923, compound

HRID 280342Notes

Reaction equation

HRID 280342 reaction equation
[C:1]([N:3]=[C:4](SC)[S:5][CH3:6])#[N:2].[NH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:27]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[N:20]=2)[CH2:14][CH2:13]1>CO>[C:1]([N:3]=[C:4]([S:5][CH3:6])[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:27]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[N:20]=2)[CH2:14][CH2:13]1)#[N:2]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 13588034HCID 13588034, compound

Product 1

HCID 178503923HCID 178503923, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.9 parts of dimethyl cyanocarbonimidodithioate, 4.8 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-3-[(4-fluorophenyl)-methyl]-3H-imidazo[4,5-b]pyridin-2-amine and 80 parts of methanol was stirred for 2 hours at room temperature. The reaction mixture was evaporated and the residue was crystallized from acetonitrile, yielding 4.5 parts (74%) of S-methyl N'-cyano-N-[2-[4-[[3-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinyl]ethyl]carbamimidothioate; mp. 172.2° C. (compound 21).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-d64dafb8663d45e5a7c973c5845f4564
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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