Hydrochloric Acid → HCID 68109819, compound

HRID 525064Notes

Reaction equation

[ClH:1].[CH2:2]([C:4]1[S:26][C:7]2[N:8]=[CH:9][N:10]=[C:11]([N:12]3[CH2:17][CH2:16][CH:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14][CH2:13]3)[C:6]=2[CH:5]=1)[CH3:3]>ClCCl>[ClH:1].[ClH:1].[CH2:2]([C:4]1[S:26][C:7]2[N:8]=[CH:9][N:10]=[C:11]([N:12]3[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]3)[C:6]=2[CH:5]=1)[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Excess hydrogen chloride gas was bubbled into a solution of tert-butyl N-(1-[6-ethylthieno[2,3-d]pyrimidin-4-yl]piperidin-4-yl)carbamate (1 g, 2.76 mmol, 1.00 equiv) in dichloromethane (20 mL). The resulting solution was stirred for 2 h at 0° C. in a water/ice bath. The resulting mixture was concentrated under vacuum to give 650 mg (70%) of 1-[6-ethylthieno[2,3-d]pyrimidin-4-yl]piperidin-4-amine dihydrochloride as a yellow solid. 1H NMR: (400 MHz, CDCl3) δ 8.61 (1H, s), 7.45 (1H, s), 5.70 (1H, s), 4.68-4.65 (2H, d), 3.43-3.37 (3H, t), 2.96-2.91 (2H, q), 2.16-2.13 (2H, d), 1.70-1.64 (2H, t), 1.29-1.26 (3H, t). MS: m/z 263 (M−2HCl+H)+.

Workup

concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-795275eae63b4beda0856a151407d8f7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340554B2

Reaction notes

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