Triethylamine → HCID 44463846, compound

HRID 1517253Notes

Reaction equation

HRID 1517253 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([Cl:27])=[C:6]([C:8]2[C:23](=[O:24])[N:22]([O:25][CH3:26])[C:11]3[N:12]=[C:13]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[N:14]=[CH:15][C:10]=3[CH:9]=2)[CH:7]=1.C([N:30](CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:59][C:60]1[CH:68]=[CH:67][C:63]([C:64](O)=[O:65])=[CH:62][C:61]=1[C:69]([F:72])([F:71])[F:70]>CN(C=O)C>[Cl:59][C:60]1[CH:68]=[CH:67][C:63]([C:64]([NH:30][C:3]2[CH:2]=[CH:7][C:6]([C:8]3[C:23](=[O:24])[N:22]([O:25][CH3:26])[C:11]4[N:12]=[C:13]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[N:14]=[CH:15][C:10]=4[CH:9]=3)=[C:5]([Cl:27])[CH:4]=2)=[O:65])=[CH:62][C:61]=1[C:69]([F:72])([F:71])[F:70]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584783586-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 44463846HCID 44463846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 6 ml maximum recovery HPLC vial equipped with a small triangular magnetic stirring bar was placed 6-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one (347 μmol). Triethylamine (344 μmol) was added, followed by aliquots of DMF stock solutions of HATU (320 μmol) and 4-chloro-3-(trifluoromethyl)benzoic acid (129 μmol), and the mixture was stirred at room temperature over night. The solutions were purified by prep. HPLC-MS. The collected fractions were transferred to centrifuge vials and lyophilized, giving 4-chloro-N-(3-chloro-4-(2-(2-(dimethylamino)ethylamino)-8-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl) -3-(trifluoromethypbenzamide as a solid (85%).

Workup

  1. customIn a 6 ml maximum recovery HPLC vial equipped with a small triangular magnetic stirring bar
  2. customThe solutions were purified by prep
  3. customgiving 4-chloro-N-(3-chloro-4-(2-(2-(dimethylamino)ethylamino)-8-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl) -3-(trifluoromethypbenzamide as a solid (85%)

Sources & evidence

ORD record
ord-269f6857823e4b32aad0270627d90ade
Source dataset
uspto-grants-2012_07
Patent number
US08232283B2

Reaction notes

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