Triethylamine → HCID 59208096, compound

HRID 2243739Notes

Reaction equation

HRID 2243739 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[C:26]([F:29])[C:27]=3[CH3:28])[C:22]([OH:24])=O)[C:13]=2[CH2:12][NH:11][C:10]1=[O:36].[F:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[C:26]([F:29])[C:27]=3[CH3:28])[C:22]([NH:42][C:41]3[CH:43]=[CH:44][C:38]([F:37])=[CH:39][CH:40]=3)=[O:24])[C:13]=2[CH2:12][NH:11][C:10]1=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59208014HCID 59208014, compound

Product 1

HCID 59208096HCID 59208096, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]-amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)-5-fluoro-4-methylbenzoic acid (25 mg, 0.05 mmol) in CH2Cl2 (2 mL) were added 4-flouroaniline (0.025 mL, 0.25 mmol), triethylamine (0.05 mL, 0.36 mmol) and HBTU (20 mg, 0.053 mmol). The reaction mixture was stirred over night. The reaction mixture was concentrated. Separation via a HPLC with TFA followed by treatment with t-amino SPE cartridge then provided the title compound as a white solid (26 mg, 88%). LC-MS m/z 594 (M+H)+; 1H-NMR (MeOD) δ 2.27 (s, 3H), 2.79 (s, 6H), 3.16 (m, 2H), 3.55 (m, 2H), 4.21 (s, 2H), 7.15 (m, 4H), 7.54 (m, 1H), 7.71 (m, 3H), 7.85 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customSeparation via a HPLC with TFA

Sources & evidence

ORD record
ord-bfea345261d44042a091718ea03d5389
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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