Hydrochloric Acid → HCID 131734882, compound

HRID 919552Notes

Reaction equation

HRID 919552 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[C:19]([NH:20][C@H:21]3[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[ClH:34]>O1CCOCC1>[ClH:34].[NH:23]1[CH2:24][CH2:25][CH2:26][C@H:21]([NH:20][C:19]2[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:3])=[O:2])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118906681HCID 118906681, compound

Product 1

HCID 131734882HCID 131734882, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of compound (S)-tert-butyl 3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (3.4 g, 7.2 mmol) in dioxane (20 mL) at 0° C., a solution of HCl in dioxane (50 mL) was added until the pH was acidic at 0° C. and stirred for 30 min. at the same temperature. The reaction mixture was concentrated in vacuo to give a residue that was triturated with ether to give (S)—N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine hydrochloride (2 g, 74%) as a free flowing solid. 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 1H), 8.32 (s, 1H), 7.98 (d, J=8.2 Hz, 2H), 7.62 (d, J=2.5 Hz, 1H), 7.42 (d, J=8.2 Hz, 2H), 7.22 (d, J=2.5 Hz, 1H), 5.80 (s, 1H), 4.29-4.25 (m, 2H), 3.38-3.32 (m, 1H), 3.19-3.12 (m, 1H), 3.00-2.97 (m, 1H), 2.35 (s, 3H), 2.01-1.95 (m, 2H), 1.75-1.69 (m, 2H). LC-MS: m/z [M+1]=372.

Workup

  1. customwas acidic at 0° C.
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a residue that
  4. customwas triturated with ether

Sources & evidence

ORD record
ord-fb123db375414d40beb67f99bd180a8d
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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