Triethylamine → HCID 118390006, compound

HRID 1478025Notes

Reaction equation

HRID 1478025 reaction equation
[Cl:1][C:2]1[C:3]([N:15]([CH3:27])[CH:16]2[CH2:26][CH2:25][C:19]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=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>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[C:3]([N:15]([CH3:27])[CH:16]2[CH2:26][CH2:25][C:19]3([CH2:24][CH2:23][N:22]([C:31](=[O:32])[CH2:30][C:28]#[N:29])[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=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 118389985HCID 118389985, compound

Product 1

HCID 118390006HCID 118390006, compoundYield 15.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension 5-chloro-N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro [5.5]undecan-9-yl)pyrimidine-2,4-diamine (165 mg, 0.42 mmol) and 2-cyanoacetic acid (107.18 mg, 1.26 mmol) in a mixture of DCM and N,N-dimethylformamide (8 mL/2 mL) were added O-(7-aza-1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (85.75 mg, 0.63 mmol) and N,N-diethylethanamine (127.50 mg, 1.26 mmol). The mixture was stirred at rt overnight and then concentrated in vacuo. 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 (30 mg, 15.54%).

Workup

  1. concentrationconcentrated 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-2553e4386a97413f9fad459ed8377ff3
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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