Hydrogen Bromide → HCID 178419913, compound

HRID 2078715Notes

Reaction equation

C(=[N:14][NH:15][C:16]1[C:17]2[CH:54]=[CH:53][CH:52]=[CH:51][C:18]=2[S:19][C:20]=1[C:21]([C:23]1[N:27](COCC2C=CC=CC=2)[C:26]2[CH:37]=[C:38]([O:41][CH2:42][CH2:43][CH2:44][N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)[CH:39]=[CH:40][C:25]=2[N:24]=1)=O)(C1C=CC=CC=1)C1C=CC=CC=1.Br>C(O)C>[N:45]1([CH2:44][CH2:43][CH2:42][O:41][C:38]2[CH:39]=[CH:40][C:25]3[N:24]=[C:23]([C:21]4[C:20]5[S:19][C:18]6[CH:51]=[CH:52][CH:53]=[CH:54][C:17]=6[C:16]=5[NH:15][N:14]=4)[NH:27][C:26]=3[CH:37]=2)[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of [3-(N′-benzhydrylidene-hydrazino)-benzo[b]thiophen-2-yl]-[1-benzyloxymethyl-6-(3-piperidin-1-yl-propoxy)-1H-benzoimidazol-2-yl]-methanone [200 mg, Intermediate (43)] and concentrated HBr (2 ml) in ethanol (4 ml) was heated at 90° C. overnight. The solution cooled to room temperature and the mixture was passed through a SCX column. Eluting with 7N ammonia in methanol yields 3-[6-(3-piperidin-1-yl-propoxy)-1H-benzoimidazol-2-yl]-1H-benzo[4,5]thieno[3,2-c]pyrazole (72.1 mg). This material was dissolved in HCl/1,4-dioxane (2 ml, 4M) and methanol (0.05 ml) and the mixture was concentrated and dried to afford 3-[6-(3-piperidin-1-yl-propoxy)-1H-benzoimidazol-2-yl]-1H-benzo[4,5]thieno[3,2-c]pyrazole hydrochloride [85.1 mg, Example 55]. LC/MS: 432 (M+H), RT=2.49 minutes; 1H NMR [(CD3)2SO]: δ9.6 (1H, s), 8.0 (1H, t), 7.4 (2H, m), 7.3 (1H, s), 7.2 (1H, m), 6.9 (1H, m), 6.8 (1H, m), 4.2 (2H, t), 3.6-3.7 (4H, m), 3.5-3.6 (2H, m), 3.4 (1H, m), 3.2 (1H, m), 2.8 (2H, m), 2.2 (2H, m), 1.8 (1H, m), 1.4 (1H, m).

Workup

temperatureThe solution cooled to room temperature
washEluting with 7N ammonia in methanol

Sources & evidence

ORD record: ord-6c22cc29e57a4753940f8c1d9016501a
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928231B2

Reaction notes

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