Triethylamine → HCID 69947548, compound

HRID 275960Notes

Reaction equation

HRID 275960 reaction equation
ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[C:22]([O:26][C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C.[CH3:41][C:42]1[C:43]([N:58]2[CH2:67][CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH:59]2[CH3:68])=[N:44][C:45]([NH:50][C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)=[N:46][C:47]=1[CH2:48]O>C(Cl)Cl>[CH3:41][C:42]1[C:43]([N:58]2[CH2:67][CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH:59]2[CH3:68])=[N:44][C:45]([NH:50][C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)=[N:46][C:47]=1[CH2:48][O:32][C:31](=[O:33])[CH2:30][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 18315695HCID 18315695, compound

Product 1

HCID 69947548HCID 69947548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-hydroxybenzotriazole(26.8 mg, 0.198 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide(32.9 mg, 0.171 mmol), N-t-butoxycarbonylglycine(27.8 mg, 0.158 mmol) and triethylamine(23.9 μl 0.171 mmol) were added to a suspension of 5-methyl-6-hydroxymethyl-2-(4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(50 mg, 0.132 mmol) in anhydrous methylene chloride(1 ml). The reaction mixture was stirred for 1 day at room temperature, washed with water. The separated organic layer was concentrated and the residual oil was purified by a silica gel column chromatography (dichloromethane/methanol 20/1) to give the titled compound.

Workup

  1. washwashed with water
  2. concentrationThe separated organic layer was concentrated
  3. customthe residual oil was purified by a silica gel column chromatography (dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-6d3acafbdd934c1f9a1d3f93be83eedc
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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