Sodium triacetoxyborohydride → (S)-1-morpholino-2-(1-((5,6,7,8-tetrahydroquinolin-8-ylamino)methyl)-9H-pyrido[3,4-b]indol-9-yl)ethanone

HRID 628671Notes

Reaction equation

HRID 628671 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:24])[CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[CH:18]=[CH:19][N:20]=[C:21]([CH:22]=O)[C:10]2=3)[CH2:3][CH2:2]1.[N:25]1[C:34]2[C@@H:33]([NH2:35])[CH2:32][CH2:31][CH2:30][C:29]=2[CH:28]=[CH:27][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:24])[CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[CH:18]=[CH:19][N:20]=[C:21]([CH2:22][NH:35][C@@H:33]4[C:34]5[N:25]=[CH:26][CH:27]=[CH:28][C:29]=5[CH2:30][CH2:31][CH2:32]4)[C:10]2=3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12031071(8S)-5,6,7,8-Tetrahydroquinolin-8-amineHCID 591766279-(2-morpholino-2-oxoethyl)-9H-pyrido[3,4-b]indole-1-carbaldehyde

Product 1

HCID 59176631(S)-1-morpholino-2-(1-((5,6,7,8-tetrahydroquinolin-8-ylamino)methyl)-9H-pyrido[3,4-b]indol-9-yl)ethanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 mmol of 9-(2-morpholino-2-oxoethyl)-9H-pyrido[3,4-b]indole-1-carbaldehyde, 1.5 mmol of (S)-5,6,7,8-tetrahydroquinolin-8-amine, and 3.00 mmol of sodium triacetoxyborohydride in 20 ml dichloromethane were stirred for 2 hours at room temperature, then reaction was quenched with saturated sodium bicarbonate solution. Organic layer was dried over magnesium sulfate, filtered off, and evaporated. Desired product was purified with column chromatography using dichloromethane:methanol:NH4OH (9:1:0.1) solvent system (85% yield). ESI+ MS: m/z (rel intensity) 456.2 (100, [M+H]+). 1H-NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=4.8 Hz), 8.36 (d, 1H, J=1.6 Hz), 8.12 (d, 1H, J=7.6 Hz), 7.92 (d, 1H, J=5.6 Hz), 7.55 (dt, 1H, J=1.2, 8.0 Hz), 7.37 (d, 1H, J=7.6 Hz), 7.29 (q, 2H, J=4.8 Hz), 7.07 (q, 1H, 4.8 Hz), 6.11 (d, 1H, J=18.0 Hz), 5.74 (d, 1H, J=17.6 Hz), 4.46 (d, 1H, J=12.0 Hz), 4.33 (d, 1H, J=12.0 Hz), 4.00 (t, 1H, J=5.6 Hz), 3.82-3.76 (m, 1H), 3.73-3.60 (m, 6H), 3.55-3.50 (m, 1H), 2.78 (t, 2H, J=6.4 Hz), 2.18-2.08 (m, 1H), 1.96-1.66 (m, 4H).

Workup

  1. customreaction
  2. customwas quenched with saturated sodium bicarbonate solution
  3. dry with materialOrganic layer was dried over magnesium sulfate
  4. filtrationfiltered off
  5. customevaporated
  6. customDesired product was purified with column chromatography

Sources & evidence

ORD record
ord-8053a0a0bc1941e0868ba0f902b49751
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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