Formaldehyde → 2-[(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-yl)-methyl-amino]-pentanoic acid [1-(1,1-dimethyl-2-Pyrrolidin-1-yl-ethyl)-1H-imidazol-4-yl]-amide

HRID 553176Notes

Reaction equation

HRID 553176 reaction equation
[CH3:1][C:2]([N:10]1[CH:14]=[C:13]([NH:15][C:16](=[O:34])[CH:17]([NH:21][CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[C:25]([F:33])[CH:26]=[C:27]([F:32])[CH:28]=3)[CH2:23]2)[CH2:18][CH2:19][CH3:20])[N:12]=[CH:11]1)([CH3:9])[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.C=O.[C:37]([BH3-])#N.[Na+]>CO>[CH3:1][C:2]([N:10]1[CH:14]=[C:13]([NH:15][C:16](=[O:34])[CH:17]([N:21]([CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[C:25]([F:33])[CH:26]=[C:27]([F:32])[CH:28]=3)[CH2:23]2)[CH3:37])[CH2:18][CH2:19][CH3:20])[N:12]=[CH:11]1)([CH3:9])[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 115473862-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [1-(1,1-dimethyl-2-Pyrrolidin-1-yl-ethyl)-1H-imidazol-4-yl]-amide

Product 1

HCID 115839652-[(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-yl)-methyl-amino]-pentanoic acid [1-(1,1-dimethyl-2-Pyrrolidin-1-yl-ethyl)-1H-imidazol-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [1-(1,1-dimethyl-2-pyrrolidin-1-yl-ethyl)-1H-imidazol-4-yl]-amide (1 equiv) is dissolved in methanol and to the reaction is added formalin (4 equiv) and sodium cyanoborohydride (2.0 equiv). The reaction is stirred at rt for 3 h, quenched with water, and extracted with methylene chloride. The solvent is dried, concentrated and the residue purified by silica gel chromatography to provide the title compound: Diagnostic C13 NMR (100 MHz, CDCl3) 55.9, 57.0, 57.1, 56.0, 65.1, 67.2, 101.0, 104.5, 110.5, 110.7, 131.1; MS m/z 488.4 (M+1).

Workup

  1. customquenched with water
  2. extractionextracted with methylene chloride
  3. customThe solvent is dried
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-7816e97e59334264a1a8f0211d2ca488
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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