Hydrochloric Acid → HCID 10184686, compound

HRID 1373800Notes

Reaction equation

HRID 1373800 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[C:15]([C:16]4[CH:21]=[C:20]([CH2:22][O:23]C5CCCCO5)[N:19]=[C:18]([NH:30][CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+].CCOCC>O1CCCC1>[CH:31]1([NH:30][C:18]2[N:19]=[C:20]([CH2:22][OH:23])[CH:21]=[C:16]([C:15]3[C:14]([C:36]4[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=4)=[N:13][N:12]4[C:7]([NH:6][CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)=[CH:8][CH:9]=[CH:10][C:11]=34)[N:17]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 10144605HCID 10144605, compound

Product 1

HCID 10184686HCID 10184686, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-cyclopentyl-3-{2-(cyclopentylamino)-6-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-pyrimidinyl}-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (134 mg, 2.23 mmol) in tetrahydrofuran (8 mL) was added hydrochloric acid (4 mL, 4 N aqueous, 32 mmol). After 30 minutes, the solution was made basic with sodium bicarbonate and ether was added. The organic layer was washed with water and brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 to 1:1 hexanes:ethyl acetate) provided {2-(cyclopentylamino)-6-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-4-pyrimidinyl}methanol (80 mg, 71%). This material was taken up in ether and treated with anhydrous hydrochloric acid in ether to yield upon filtration a yellow solid. 1H NMR of hydrochloride salt (CDCl3) δ 8.00–7.94 (broad, 1H), 7.78 (d, 1H), 7.54–7.44 (m, 3H), 7.17 (m, 2H), 6.22 (s, 1H), 6.19 (d, 1H), 6.07 (d, 1H), 4.74–4.60 (broad, 1H), 4.47 (s, 2H), 4.36 (m, 1H), 3.99 (m, 1H), 2.16–2.00 (m, 4H), 1.82–1.59 (m, 12H); 19F NMR (CDCl3) δ −111.26; MS m/z 487 (M+1 of free base).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-698d07396e2f4c2ab4f65574f40c8e5a
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

Loading…