6-Aminobenzothiazole → Benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride

HRID 2375827Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([Cl:22])[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[S:24]1[C:28]2[CH:29]=[C:30]([NH2:33])[CH:31]=[CH:32][C:27]=2[N:26]=[CH:25]1>C(O)CCC>[ClH:22].[ClH:22].[ClH:22].[S:24]1[C:28]2[CH:29]=[C:30]([NH:33][C:21]3[C:16]4[CH:15]=[C:14]([C:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH:12]=5)[NH:23][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:31]=[CH:32][C:27]=2[N:26]=[CH:25]1

Participants

Conditions

Temperature: 115 °C

Procedure

Alternative preparation: A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (5.02 g, 15 mmol) and 1,3-benzothiazol-6-amine (2.25 g, 15 mmol) in 1-butanol (50 mL) was heated at 115° C. overnight, LC-MS showed the desired product and some de-Boc product. After the mixture was cooled to rt, it was diluted with hexane (50 mL), the gray solid was collected by filtration, a mixture of the desired product and some de-Boc product, which was directly used in the next step. To a suspension of this material in methylene chloride (30 mL) was added 4M HCl/1,4-dioxane (30 mL), the resulting mixture was stirred at rt for 5 h. The mixture was then diluted with CH2Cl2 (30 mL), and the light-yellow solid was collected by filtration and dried in vacuo.

Workup

customAlternative preparation

Sources & evidence

ORD record: ord-4debc5401e314303a26fa1be90b73bf1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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