Benzylamine → 2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-(4-methoxybenzyl)ethanamine

HRID 590835Notes

Reaction equation

HRID 590835 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.C(N)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[C:44](O[BH-](OC(=O)C)OC(=O)C)(=[O:46])C.[Na+]>CCO.CC(O)=O.ClCCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][C:40]2[CH:41]=[CH:42][C:37]([O:46][CH3:44])=[CH:38][CH:39]=2)[C:5]2[C:13]([I:35])=[N:14][N:15]([C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 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 1182724142-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-(4-methoxybenzyl)ethanamine

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 (2.2 g, 3.73 mmol) and benzylamine (1.02 g, 7.46 mmol) were stirred in a 3:1:1 solution of DCE:AcOH:EtOH (10 ml) at 85° C. for 3 hrs. Solvent removed by vacuum and residue taken in DCE (15 ml), added sodium triacetoxyborohydride (3.16 g, 14.9 mmol), acetic acid (0.9 g, 14.9 mmol) and stirred at room temperature for 6 hours. Reaction 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 (0-10% MeOH-EtOAc) gave 2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-(4-methoxybenzyl)ethanamine MS ESI calc'd. for C34H28ClIN4 [M+H]+ 685. found 685.

Workup

  1. customSolvent removed by vacuum and residue
  2. customReaction
  3. customwas partitioned between DCM and aqueous sodium bicarbonate
  4. customthe organics was separated
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the residue by flash column (0-10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-292914502f3a4c42b179958cd27cb082
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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