Triethylamine → HCID 25105792, compound

HRID 1675351Notes

Reaction equation

HRID 1675351 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:12][C:11]([N:13]2[CH2:20][C:19]3[CH2:18][NH:17][CH2:16][C:15]=3[CH2:14]2)=[N:10][CH:9]=1)=[O:7].FC(F)(F)C([O-])=O.C(N(CC)CC)C.Cl[C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]=[CH:39][N:38]=1>CN(C=O)C>[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:12][C:11]([N:13]2[CH2:14][C:15]3[CH2:16][N:17]([C:37]4[C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[N:40]=[CH:39][N:38]=4)[CH2:18][C:19]=3[CH2:20]2)=[N:10][CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 788644-ChloroquinazolineHCID 84468TrifluoroacetateHCID 58459774HCID 58459774, compound

Product 1

HCID 25105792HCID 25105792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-Methylbutyl)-2-(3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)thiazole-5-carboxamide, trifluoroacetate (220 mg, 0.52 mmol) and triethylamine (0.22 ml, 1.57 mmol) were dissolved in 10 ml of DMF and admixed in an ice bath with 4-chloroquinazoline (172 mg, 1 mmol). The mixture was stirred further for 1 h and allowed to warm to room temperature, and concentrated, water and ethyl acetate were added and the organic phase was removed, concentrated by evaporation and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). M+H+: 435.05.

Workup

  1. concentrationconcentrated
  2. additionwater and ethyl acetate were added
  3. customthe organic phase was removed
  4. concentrationconcentrated by evaporation
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-22ba69018a974bbfbf682804bf05e35a
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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