Triethylamine → HCID 44540982, compound

HRID 244723Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7](O)=[O:8])=[C:5]([CH3:10])[CH:4]=[N:3]1.ClC(N(C)C)=C(C)C.[NH:19]1[C:27]2[C:22](=[C:23]([C:28]3[CH:29]=[C:30]([NH2:37])[C:31]4[CH:32]=[N:33][NH:34][C:35]=4[CH:36]=3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.C(N(CC)CC)C>C(Cl)Cl>[NH:19]1[C:27]2[C:22](=[C:23]([C:28]3[CH:36]=[C:35]4[C:31]([CH:32]=[N:33][NH:34]4)=[C:30]([NH:37][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[CH:4][C:5]=4[CH3:10])=[O:8])[CH:29]=3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 1,4-dimethyl-1H-pyrazole-5-carboxylic acid (21 mg) in dry DCM (10 ml) was treated with 1-chloro-N,N,2-trimethyl-1-propen-1-amine (0.02 ml) and allowed to stir at 20° C. for 10 min when a solution of 6-(1H-indol-4-yl)-1H-indazol-4-amine (25 mg) and triethylamine (0.028 ml) in DCM (5 ml) was added and the mixture stirred at 20° C. for 18 h. The mixture was poured onto an aminopropyl SPE cartridge (1 g) and allowed to stand for 2 h, then the mixture was eluted with methanol (5 ml) and blown to dryness under a stream of nitrogen and purified by mass directed preparative HPLC (Method A) to give the title compound (6 mg) as a white solid.

Workup

additionwas added
waitto stand for 2 h
washthe mixture was eluted with methanol (5 ml)
custompurified by mass

Sources & evidence

ORD record: ord-8cb4fc357d6946729935ccfa799e5920
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658635B2

Reaction notes

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