Ethyl isocyanate → HCID 178465344, compound

HRID 2052995Notes

Reaction equation

HRID 2052995 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:4]1.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32]>C(#N)C>[NH2:16][C:15]1[C:10]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8][N:7]([C@H:5]3[CH2:4][C@H:3]([CH2:2][NH:1][C:34]([NH:33][CH2:31][CH3:32])=[O:35])[CH2:6]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 178511295HCID 178511295, compound

Product 1

HCID 178465344HCID 178465344, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 50 mg (0.125 mmol) of trans-7-(3-aminomethyl-cyclobutyl)-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine in 4 ml of dry acetonitrile is added at RT 16 μl (0.2 mmol) of ethyl isocyanate (Fluka, Buchs, Switzerland). After stirring for 16 h at RT, working-up is effected by partitioning between water and ethyl acetate. The organic layer is dried over magnesium sulfate and evaporated to dryness to provide trans-1-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-3-ethyl-urea. Analytical HPLC: tR=6.77 min (Grad 2); ES-MS: m/eo=471.1.

Workup

  1. customby partitioning between water and ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-a7fdac0236d3473b9ad91de27ee9564c
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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