Hydrochloric Acid → HCID 69430048, compound

HRID 915854Notes

Reaction equation

HRID 915854 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]1[C:16]2[C:17](=[C:21]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[N:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:23]=2)[N:18]=[CH:19][N:20]=1)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:30].[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:21]2[N:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:23]=[C:16]3[C:15]([N:11]4[CH2:10][CH:9]5[CH2:14][CH:12]4[CH2:13][NH:8]5)=[N:20][CH:19]=[N:18][C:17]=23)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11478201HCID 11478201, compound

Product 1

HCID 69430048HCID 69430048, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the solution of 5-[3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 2A-46 (595 mg, 1.11 mmol) in dioxane (8 ml) was added HCl (2.22 ml, 4 N in dioxane, 8.88 mmol). The reaction mixture was stirred for 3 hours under nitrogen at room temperature. Then, the reaction mixture was concentrated and co-evaporated with diethyl ether (25 ml). The residue was further dried in a drying pistol under vacuum at 65° C. to give Rac-(S,S)-3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2H-pyrazolo[4,3-d]pyrimidine HCl salt 4A-1 (522 mg, 92%): MS: 437.1 (M+1)+; 1H NMR (400 MHz, CD3OD) δ 8.6 (d, J=6.2 Hz, 1H), 7.7 (dd, J=15.8, 7.1 Hz, 1H), 7.6 (m, 2H), 7.5 (m, 1H), 7.4 (dd, J=8.3, 3.3 Hz, 2H), 7.3 (t, J=7.5 Hz, 2H), 6.3 (s, 0.5H), 5.8 (s, 0.5H), 4.7 (m, 1H), 4.6 (d, J=13.7 Hz, 0.5H), 4.5 (dd, J=13.7, 2.5 Hz, 0.5H), 4.2 (ddd, J=29.5, 14.1, 1.7 Hz, 1H), 3.6 (m, 2H), 2.5 (dd, J=24.0, 12.0 Hz, 1H), 2.3 (t, J=11.2 Hz, 1H).

Workup

  1. concentrationThen, the reaction mixture was concentrated and co-evaporated with diethyl ether (25 ml)
  2. customThe residue was further dried in a drying pistol under vacuum at 65° C.

Sources & evidence

ORD record
ord-700fa11ad3c94ef881e531c53eff22d8
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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