Hydrochloric Acid → HCID 86589652, compound

HRID 1006368Notes

Reaction equation

HRID 1006368 reaction equation
[ClH:1].Cl.Cl.[CH:4]([C@H:17]1[N:22]2[CH2:23][CH2:24][NH:25][CH2:26][C@H:21]2[CH2:20][N:19]([CH2:27][C:28]2[CH:33]=[C:32]([N:34]3[C:38]([C:39]([F:42])([F:41])[F:40])=[N:37][N:36]=[N:35]3)[CH:31]=[CH:30][C:29]=2[O:43][CH3:44])[CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[C:77](OCC)(=[O:79])C>ClCCl.O.C(O)=O>[ClH:1].[ClH:1].[CH:4]([C@H:17]1[N:22]2[CH2:23][CH2:24][N:25]([CH:77]=[O:79])[CH2:26][C@H:21]2[CH2:20][N:19]([CH2:27][C:28]2[CH:33]=[C:32]([N:34]3[C:38]([C:39]([F:42])([F:41])[F:40])=[N:37][N:36]=[N:35]3)[CH:31]=[CH:30][C:29]=2[O:43][CH3:44])[CH2:18]1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86589651HCID 86589651, compound

Product 1

HCID 86589652HCID 86589652, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Formic acid (28 μl ) was added to a mixture of (4R,9aS)-4-benzhydryl-2-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]octahydro-2H-pyrazino[1,2-a]pyrazine trihydrochloride (100 mg), N,N-diisopropylethylamine (129 μl), 1-hydroxybenzotriazole (30.1 mg) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (34.2 mg) in dichloromethane (2.0 ml). After being stirred for 18 hours at room temperature, the resulting mixture was poured into water, and the whole was extracted with ethyl acetate, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and methanol (20:1). The fractions containing the objective compound was collected and evaporated under reduced pressure and resulting residue was treated with 4N hydrogen chloride in ethyl acetate to give (6R,9aR)-6-benzhydryl-8-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]octahydro-2H-pyrazino[1,2-a]pyrazine-2-carbaldehyde dihydrochloride (100.1 mg) as colourless powder.

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. additionThe fractions containing the objective compound
  6. customwas collected
  7. customevaporated under reduced pressure
  8. customresulting residue

Sources & evidence

ORD record
ord-f3cf18b36d8d45d0889cc06e30a90cfb
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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