Ethyl isocyanate → HCID 53379666, compound

HRID 1771564Notes

Reaction equation

HRID 1771564 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=1)[CH2:2]2.C(N(CC)CC)C.[CH2:29]([N:31]=[C:32]=[O:33])[CH3:30]>C(Cl)Cl>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:21]=[CH:20][C:18]([NH:19][C:32]([NH:31][CH2:29][CH3:30])=[O:33])=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 67382726HCID 67382726, compound2×

Product 1

HCID 53379666HCID 53379666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-4-yl)aniline (intermediate 26) (100 mg, 0.354 mmol) was stirred with triethylamine (74 μl, 0.532 mmol) and ethylisocyanate (42 μl, 0.531 mmol) in DCM (2 ml) overnight. The reaction mixture was concentrated in vacuo and then purified by prep HPLC at low pH. (24 mg, 19%)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by prep HPLC at low pH

Sources & evidence

ORD record
ord-362489fb8f554e73b8a339d5164fef20
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

Loading…