Carbon Disulfide → HCID 15037422, compound

HRID 1886419Notes

Reaction equation

HRID 1886419 reaction equation
[C:1](=[S:3])=S.[NH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:21]([CH2:22][C:23]3[O:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=2)[CH2:8]1>O1CCCC1>[N:4]([CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:21]([CH2:22][C:23]3[O:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=2)[CH2:8]1)=[C:1]=[S:3]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 15037416HCID 15037416, compound

Product 1

HCID 15037422HCID 15037422, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 4.2 parts of N,N-methyltetraylbis[cyclohexanamine] and 90 parts of tetrahydrofuran were added 10.6 parts of carbon disulfide. After stirring for 10 minutes, a solution of 6 parts of N-[1-(2-aminoethyl)-3-pyrrolidinyl]-3-[(5-methyl-2-furanyl)methyl]-3H-imidazo-[4,5-b]pyridin-2-amine in 36 parts of tetrahydrofuran was added dropwise to the thus obtained mixture (exothermic reaction, the temperature rose to 26° C.). Upon complete addition, stirring was continued for 30 minutes at room temperature. The reaction mixture was evaporated and the residue was taken up in 240 parts of acetonitrile. The precipitate was filtered off and the filtrate was evaporated, yielding 6.9 parts (100%) of N-[1-(2-isothiocyanatoethyl)-3-pyrrolidinyl]-3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine as a residue (compound 171).

Workup

  1. customexothermic reaction
  2. customrose to 26° C.
  3. additionUpon complete addition
  4. stirringstirring
  5. waitwas continued for 30 minutes at room temperature
  6. customThe reaction mixture was evaporated
  7. filtrationThe precipitate was filtered off
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d19111a3626e421cba8761bac6308369
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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