Triethylamine → HCID 178483474, compound

HRID 2236813Notes

Reaction equation

HRID 2236813 reaction equation
Cl.[CH3:2][N:3]([CH3:10])[CH2:4][CH:5]=[CH:6][C:7](O)=[O:8].CCN(CC)CC.C(OC(Cl)=O)C(C)C.[I:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33](=[O:37])[NH:32][C:31](=[O:38])[C:30]2=[CH:39][NH:40][C:41]1[CH:46]=[CH:45][C:44]([CH:47]2[CH2:51][CH2:50][CH2:49][NH:48]2)=[CH:43][CH:42]=1>CN(C)C=O>[CH3:2][N:3]([CH3:10])[CH2:4][CH:5]=[CH:6][C:7]([N:48]1[CH2:49][CH2:50][CH2:51][CH:47]1[C:44]1[CH:45]=[CH:46][C:41]([NH:40][CH:39]=[C:30]2[C:29]3[C:34](=[CH:35][CH:36]=[C:27]([I:26])[CH:28]=3)[C:33](=[O:37])[NH:32][C:31]2=[O:38])=[CH:42][CH:43]=1)=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 53395244(E)-4-(diMethylaMino)but-2-enoic acidHCID 178518339HCID 178518339, compound

Product 1

HCID 178483474HCID 178483474, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Dimethylamino-but-2-enoic acid hydrochloride salt (66 mg, 0.40 mmol) in N,N-dimethylformamide (1 mL) is treated with Et3N (0.06 mL) at 0° C. To the mixture is then added isobutylchloroformate (0.05 mL). The mixture is then stirred at this temperature for 30 min before addition of 6-Iodo-4-[(4-pyrrolidin-2-yl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione (80 mg, 0.17 mmol) in N,N-dimethylformamide (3 mL) dropwisely and the reaction is allowed to stir at room temperature overnight. After an aqueous workup, the final residue is purified with prep-TLC to afford the title compound (20 mg, 21%). 1H NMR (400 MHz, DMSO) δ12.52 (1H, d, J=12.4 Hz), 11.39-11.41 (1H, m), 8.90-8.94 (1H, m), 8.59 (1H, m), 7.21-7.75 (6H, m), 6.48-6.59 (1.4H, m), 6.01-6.05 (0.6H, m), 5.1-5.24 (1H, m), 3.57-3.91 (2H, m), 3.06-3.07 (1H, m), 2.82-2.84 (1H, m), 2.1-2.39 (2H, m), 2.18 (3H, s), 1.96 (3H, s), 1.77-1.95 (2H, m). MS (ESI): 571.0 (M+1)+1.

Workup

  1. customAfter an aqueous workup, the final residue is purified with prep-TLC

Sources & evidence

ORD record
ord-c1df7303adaf4dcea71079d0bbed2092
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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