Triethylamine → HCID 59208021, compound

HRID 2243744Notes

Reaction equation

HRID 2243744 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](S(C)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:22]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37].[CH3:38][N:39]([CH3:43])[CH2:40][CH2:41][NH2:42].C(N(CC)CC)C>ClCCl>[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:42][CH2:41][CH2:40][N:39]([CH3:43])[CH3:38])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:22]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 11950818HCID 11950818, compound

Product 1

HCID 59208021HCID 59208021, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide (30 mg, 0.055 mmol) in dichloromethane (3.0 mL) were added N,N-dimethyl-1,2-ethanediamine (12.2 μL, 0.11 mmol) and triethylamine (15.6 μL, 0.11 mmol). The reaction mixture was stirred at room temperature for 16 hours then was concentrated, redissolved in DMSO (0.5 mL), filtered and applied to the reverse phase HPLC to afford the titled compound 16.9 mg (54%). LC-MS m/z 565 (M+H)+; 1H-NMR (MeOD) 2.20 (s, 3H), 2.33 (m, 7H), 2.81 (s, 2H), 3.26 (m, 1H), 4.13 (m, 1H), 4.43 (s, 1H), 7.17 (m, 3H), 7.50 (m, 3H), 8.01 (m, 2H).

Workup

  1. concentrationthen was concentrated
  2. dissolutionredissolved in DMSO (0.5 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-fd148647c00a40ba921db49beec3b644
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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