Ethylamine hydrochloride → 2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-ethylethanamine

HRID 590846Notes

Reaction equation

HRID 590846 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[CH:9]/[N:10](C)[CH3:11])[C:5]2[C:13]([I:35])=[N:14][N:15]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[CH:3]=1.Cl.[CH2:37](N)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCO.CC(O)=O.ClCCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][CH3:37])[C:5]2[C:13]([I:35])=[N:14][N:15]([C:16]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 118272432(E)-2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N,N-dimethylethenamine

Product 1

HCID 1182722402-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-ethylethanamine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent

Procedure

(E)-2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N,N-dimethylethenamine (1.0 g, 1.692 mmol) and ethanamine HCl (0.552 g, 6.77 mmol) were stirred in a 3:1:1 solution of DCE:AcOH:EtOH (5 ml) at 100° C. for 2 hrs. Solvent was removed by vacuum and the residue was taken in DCE (15 ml) and treated with sodium triacetoxyborohydride (0.9 g, 4.23 mmol), acetic acid (0.4 g, 6.7 mmol) and stirred at room temperature for 6 hours. The eaction mixture was partitioned between DCM and aqueous sodium bicarbonate and the organics was separated, washed with brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-15% MeOH-DCM) gave 2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-ethylethanamine. MS ESI calc'd. for C29H26ClIN4 [M+H]+ 593. found 593.

Workup

  1. customSolvent was removed by vacuum
  2. customThe eaction mixture was partitioned between DCM and aqueous sodium bicarbonate
  3. customthe organics was separated
  4. washwashed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the residue by flash column (0-15% MeOH-DCM)

Sources & evidence

ORD record
ord-02b1debd8b0b463783106d81d1626ab0
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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