Nitrogen → 4-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzonitrile

HRID 251296Notes

Reaction equation

HRID 251296 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]([CH2:24][C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH:14]1[C:23]2[N:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1.[Li+].[BH4-].N#N>CO>[CH3:31][C:30]1[C:25]([CH2:24][N:13]([CH2:12][C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH2:3][OH:2])[CH:14]2[C:23]3[N:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:17][CH2:16][CH2:15]2)=[N:26][CH:27]=[C:28]([CH3:32])[CH:29]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 4148881Lithium borohydrideHCID 672726215-Cyano-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8yl)amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 672718954-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-cyano-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8yl)-amino]-methyl}-benzoic acid methyl ester (6.29 g, 14.3 mmol) dissolved in MeOH (72 mL) was added LiBH4 (3.1 g, 0.14 mmol). The mixture was stirred for 18 hours under a positive pressure of N2. The mixture was concentrated in vacuo and redissolved in CH2Cl2 (75 mL). A saturated solution of NaHCO3 (75 mL) was added. Extract with CH2Cl2 (2×50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to afford 4-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzonitrile as an off white foam (5.82 g, 99%). 1H NMR (CDCl3) δ 1.62 (m, 1H), 2.02 (m, 1H), 2.13 (m, 1H), 2.18 (s, 3H), 2.26 (s, 3H), 2.68 (m, 1H), 2.81 (m, 1H), 3.82 (m, 4H), 4.23 (m, 3H), 7.06 (dd, 1H, J=7.0, 5.7 Hz), 7.36 (d, 2H, J=7.5 Hz), 7.44 (m, 2H), 7.65 (s, 1H), 8.17 (s, 1H), 8.37 (d, 1H, J=3.9 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in CH2Cl2 (75 mL)
  3. additionA saturated solution of NaHCO3 (75 mL) was added
  4. extractionExtract with CH2Cl2 (2×50 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9608238f7b3d4d4b92f1284283c8368f
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…