Ethyl isocyanate → (S)-1-ethyl-3-(5-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)thiazol-2-yl)urea

HRID 1626618Notes

Reaction equation

HRID 1626618 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]3[CH3:18])=[N:7][C:6]([C:19]3[S:23][C:22]([NH2:24])=[N:21][CH:20]=3)=[N:5][C:4]=2[CH2:3]1.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26]>>[CH2:25]([NH:27][C:28]([NH:24][C:22]1[S:23][C:19]([C:6]2[N:7]=[C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]3[CH3:18])[C:9]3[CH2:10][CH2:11][N:2]([CH3:1])[CH2:3][C:4]=3[N:5]=2)=[CH:20][N:21]=1)=[O:29])[CH3:26]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 86663160(S)-5-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)thiazol-2-amine

Product 1

HCID 86663161(S)-1-ethyl-3-(5-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)thiazol-2-yl)ureaYield 11%

Procedure

The product from step 1 was treated as described for example 85 with ethyl isocyanate. The mixture was concentrated in vacuo and the material purified by prep HPLC at high and low pH, yielding the title compound (15.5 mg, 0.037 mmol, 11% over 2 steps).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe material purified by prep HPLC at high and low pH

Sources & evidence

ORD record
ord-2f21ae71f13e46b9ad27e965921d8aab
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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