Ethyl isocyanate → HCID 46913169, compound

HRID 1626601Notes

Reaction equation

HRID 1626601 reaction equation
Cl.[CH2:2]([NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[C:17]3[CH2:23][CH2:22][NH:21][CH2:20][C:18]=3[N:19]=2)=[CH:10][CH:9]=1)=[O:6])[CH3:3].CCN(C(C)C)C(C)C.[CH2:40]([N:42]=[C:43]=[O:44])[CH3:41]>C(Cl)Cl>[CH2:40]([NH:42][C:43]([N:21]1[CH2:22][CH2:23][C:17]2[C:16]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])=[N:15][C:14]([C:11]3[CH:10]=[CH:9][C:8]([NH:7][C:5]([NH:4][CH2:2][CH3:3])=[O:6])=[CH:13][CH:12]=3)=[N:19][C:18]=2[CH2:20]1)=[O:44])[CH3:41]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 66687899HCID 66687899, compound

Product 1

HCID 46913169HCID 46913169, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride (example 13 as a hydrochloride salt) (99 mg, 0.25 mmol) in DCM (3 mL) at room temperature (20° C.) was added DIPEA (44 uL, 0.26 mmol) followed by ethyl isocyanate (22 uL, 0.27 mmol). The reaction mixture was stirred overnight. The solvent was removed in vacuo and the residue purified by prep HPLC (low pH) to afford a brown solid (55 mg, 47%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-d0574cdfb72f4e348df8da8db2aca9bc
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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