p-Toluenesulfonic acid → 5-[4-(1-Benzyl-1H-indol-5-ylamino)-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amide hydrochloride

HRID 1072147Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]([CH:17]=[C:18]3[C:26]4[C:25]([Cl:27])=[N:24][CH:23]=[N:22][C:21]=4[NH:20][C:19]3=[O:28])=[CH:15][CH:16]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:29]([N:36]1[C:44]2[C:39](=[CH:40][C:41]([NH2:45])=[CH:42][CH:43]=2)[CH:38]=[CH:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>COCCOCCOC>[ClH:27].[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]([CH:17]=[C:18]3[C:26]4[C:25]([NH:45][C:41]5[CH:40]=[C:39]6[C:44](=[CH:43][CH:42]=5)[N:36]([CH2:29][C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:37]=[CH:38]6)=[N:24][CH:23]=[N:22][C:21]=4[NH:20][C:19]3=[O:28])=[CH:15][CH:16]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 177.5 °C

Procedure

A mixture of 5-(4-chloro-6-oxo-6.7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide, 1-benzyl-1H-indol-5-ylamine and p-toluenesulfonic acid (5 mg) in 2 mL of 1-methyl-2-pyrrodinone and 2-methoxyethyl ether (1:3) was heated at 170-185° C. for 7 to 15 hours. The reaction mixture was evaporated to dryness and purified by reversed phase HPLC, then dissolved in 2N HCl and acetontrile and freeze-dried to give 13.5 mg (42%) of the title compound. MS 589.3 [M++1].

Workup

customThe reaction mixture was evaporated to dryness
custompurified by reversed phase HPLC
dissolutiondissolved in 2N HCl
customacetontrile and freeze-dried

Sources & evidence

ORD record: ord-8f69d0a43ea34f6a85541e93aa2f72ea
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908930B2

Reaction notes

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