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Triethylamine → 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyridin-2-ylmethyl)pyrimidine-5-formamide

HRID 2200869
Notes
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Reaction equation

HRID 2200869 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:40]12[CH2:45][CH:44]1[CH2:43][N:42]([C:46]1[N:51]=[C:50]([NH:52][CH2:53][C:54]3[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[C:56]([Cl:62])[CH:55]=3)[C:49]([C:63](O)=[O:64])=[CH:48][N:47]=1)[CH2:41]2>C1COCC1>[CH:44]12[CH2:45][CH:40]1[CH2:41][N:42]([C:46]1[N:51]=[C:50]([NH:52][CH2:53][C:54]3[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[C:56]([Cl:62])[CH:55]=3)[C:49]([C:63]([NH:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[O:64])=[CH:48][N:47]=1)[CH2:43]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1176225452-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

Product 1

HCID 73214472
2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyridin-2-ylmethyl)pyrimidine-5-formamide
Yield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (50 mL) were dissolved 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid, pyridine-2-ylmethylamine (69 mg, 0.64 mmol) and triethylamine (0.2 mL). The solution was cooled in an ice bath and HATU (266 mg, 0.70 mmol) was then added. The reaction was conducted at ambient temperature for 18 h. The reaction mixture was concentrated, followed by addition of water and extraction with ethyl acetate. The organic phase was dried, concentrated and purified by silica gel column chromatography (DCM/methanol=50/1) to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyridin-2-ylmethyl)pyrimidine-5-formamide (60 mg, 24% yield).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. concentrationThe reaction mixture was concentrated
  3. additionfollowed by addition of water and extraction with ethyl acetate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (DCM/methanol=50/1)

Sources & evidence

ORD record
ord-e7b917f0565b461c974aa39589b7b99e
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359371B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes