Triethylamine → HCID 118390096, compound

HRID 1478021Notes

Reaction equation

HRID 1478021 reaction equation
[CH3:1][N:2]([CH:17]1[CH2:27][CH2:26][C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:19][CH2:18]1)[C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([NH:10][C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)[N:4]=1.[C:28]([CH2:30][C:31](O)=[O:32])#[N:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:1][N:2]([C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([NH:10][C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)[N:4]=1)[CH:17]1[CH2:27][CH2:26][C:20]2([CH2:25][CH2:24][N:23]([C:31](=[O:32])[CH2:30][C:28]#[N:29])[CH2:22][CH2:21]2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131736500HCID 131736500, compound

Product 1

HCID 118390096HCID 118390096, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N4,5-dimethyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (93 mg, 0.25 mmol) and 2-cyanoacetic acid (63.8 mg, 0.75 mmol) in a mixture of dichloromethane and N,N-dimethylformamide (8 mL/2 mL) were added O-(7-aza-1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluoro phosphate (51.72 mg, 0.38 mmol) and N,N-diethylethanamine (75.9 mg, 0.75 mmol). The mixture was stirred at rt overnight then concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1) to give the title compound as a yellow solid (40 mg, 36.38%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1)

Sources & evidence

ORD record
ord-b283d0d97d814174b0fe373be3596643
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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