Hydrochloric Acid → HCID 131726761, compound

HRID 2054420Notes

Reaction equation

HRID 2054420 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]1[N:20]2[N:21]=[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:23]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[C:19]2[N:18]=[C:17]([CH3:38])[N:16]=1)=O)(C)(C)C.Cl.C(OCC)C>C(Cl)Cl.CO>[ClH:30].[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:22]1[C:23]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[C:19]2[N:18]=[C:17]([CH3:38])[N:16]=[C:15]([N:11]3[CH2:10][C@@H:9]4[CH2:14][C@H:12]3[CH2:13][NH:8]4)[N:20]2[N:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59655724HCID 59655724, compound

Product 1

HCID 131726761HCID 131726761, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,4S)-5-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (8A-1; 200 mg, 0.36 mmol) in methylene chloride (3 ml) and methanol (3 ml) was added 1M HCl in diethyl ether (1.8 ml, 1.8 mmol). After stirring overnight, the reaction was concentrated, in vacuo, and then triturated from diethyl ether to afford 9A-1 (180 mg, 96%) as a solid: +ESI MS (M+1) 451.3; 1H NMR (400 MHz, CD3OD) δ 7.48-7.36 (m, 4H), 7.32 (d, J=8.7 Hz, 2H), 7.26 (d, J=8.7 Hz, 2H), 4.64 (s, 1H), 3.68 (d, J=10.8 Hz, 1H), 3.55 (dd, J=10.8, 1.6 Hz, 1H), 2.58 (s, 3H), 2.41 br d, J=11.2 Hz, 1H), 2.18 (d, J=11.2 Hz, 1H).

Workup

  1. concentrationthe reaction was concentrated, in vacuo
  2. customtriturated from diethyl ether
  3. customto afford 9A-1 (180 mg, 96%) as a solid

Sources & evidence

ORD record
ord-73b941dc48214c3dbb2ab2f162d7c39a
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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