Triethylamine → N-(2-Cyclopropylethyl)-2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo-[3,4-c]pyrrol-2-yl]thiazole-5-carboxamide

HRID 1675345Notes

Reaction equation

HRID 1675345 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][C:4]=1[C:5]([N:7]1[CH2:11][C:10]2[CH2:12][N:13]([C:15]3[S:16][C:17]([C:20](O)=[O:21])=[CH:18][N:19]=3)[CH2:14][C:9]=2[CH2:8]1)=[O:6].[Li].Cl.[CH:31]1([CH2:34][CH2:35][NH2:36])[CH2:33][CH2:32]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH:31]1([CH2:34][CH2:35][NH:36][C:20]([C:17]2[S:16][C:15]([N:13]3[CH2:14][C:9]4[CH2:8][N:7]([C:5](=[O:6])[C:4]5[CH:23]=[CH:24][CH:25]=[CH:26][C:3]=5[C:2]([F:28])([F:1])[F:27])[CH2:11][C:10]=4[CH2:12]3)=[N:19][CH:18]=2)=[O:21])[CH2:33][CH2:32]1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 3028194LithiumHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219160802-Cyclopropylethanamine hydrochlorideHCID 593609132-[5-(2-Trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl]thiazole-5-carboxylic acid

Product 1

HCID 25105789N-(2-Cyclopropylethyl)-2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo-[3,4-c]pyrrol-2-yl]thiazole-5-carboxamide

Procedure

2-[5-(2-Trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl]thiazole-5-carboxylic acid, lithium salt (88 mg, 0.212 mmol), 2-cyclopropylethylamine hydrochloride (38.7 mg, 0.318 mmol), triethylamine (126 μl, 0.92 mmol) and HATU (128 mg, 0.37 mmol) were stirred at room temperature for 2 h. The solvent was evaporated off and the residue was purified by preparative HPLC (PR18, acetonitrile/water, 0.1% TFA). Yield: 6 mg (6%), M+H+: 477.19.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was purified by preparative HPLC (PR18, acetonitrile/water, 0.1% TFA)

Sources & evidence

ORD record
ord-3d02ee171afd4a9e9a862b47bca52693
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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