Hydrochloric Acid → HCID 68110255, compound

HRID 525066Notes

Reaction equation

HRID 525066 reaction equation
[ClH:1].[CH2:2]([C:4]1[S:27][C:7]2[N:8]=[CH:9][N:10]=[C:11]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][NH:19]C(=O)OC(C)(C)C)[CH2:14][CH2:13]3)[C:6]=2[CH:5]=1)[CH3:3]>ClCCl>[ClH:1].[CH2:2]([C:4]1[S:27][C:7]2[N:8]=[CH:9][N:10]=[C:11]([N:12]3[CH2:13][CH2:14][CH:15]([CH2:18][NH2:19])[CH2:16][CH2:17]3)[C:6]=2[CH:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68109751HCID 68109751, compound

Product 1

HCID 68110255HCID 68110255, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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)methyl]carbamate (3.4 g, 9.03 mmol, 1.00 equiv) in dichloromethane (30 mL). The resulting solution was stirred for 2 h at room temperature. The product was precipitated and collected by filtration. The solid was dried in an oven under reduced pressure to give 2.5 g (88%) of Compound I-178 as a yellow solid. 1H NMR: (400 MHz, CD3OD) δ 8.59 (1H, s), 7.46 (1H, s), 4.90-4.95 (2H, d), 3.44-3.50 (2H, t), 3.02-3.07 (2H, q), 2.94-2.95 (2H, d), 2.16-2.21 (1H, m), 2.06-2.09 (2H, d), 1.49-1.55 (2H, q), 1.39-1.43 (3H, t). MS: m/z 277 (M+H)+.

Workup

  1. customThe product was precipitated
  2. filtrationcollected by filtration
  3. customThe solid was dried in an oven under reduced pressure

Sources & evidence

ORD record
ord-6873f2fb4777452bbb789d29027c02ec
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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