Triethylamine → HCID 91827621, compound

HRID 1500080Notes

Reaction equation

HRID 1500080 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[NH:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:18]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CS(C)=O.C(OCC)(=O)C>[C:18]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:19]=[CH:20][C:21]([CH2:24][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[NH:13][C:12](=[O:17])[NH:11][CH2:10]4)[CH2:2][CH2:3]2)=[CH:22][CH:23]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118307490HCID 118307490, compound

Product 1

HCID 91827621HCID 91827621, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 6 (0.15 g, 0.43 mmol) and biphenyl-4-carbaldehyde a (0.1 g, 0.55 mmol) in DMSO (2 mL) at 0° C. was added Et3N (0.13 mL, 0.97 mmol). After being stirred for 0.5 h at room temperature, NaBH(OAc)3 (0.11 g, 0.53 mmol) was added and the mixture was stirred for 6 h. The reaction was added sat. NaHCO3 solution (5 mL) and stirred for 15 min, followed by the addition of ethyl acetate (20 mL). The organic layer was separated and washed with sat. NaHCO3, brine, and dried over Na2SO4 and evaporated. Column chromatography on silica gel, eluting with methanol:dichloromethane (5:95) and then changing (10:90) afforded 0.102 g (60%) of compound 6a as an off-white solid. IR (KBr) νmax. cm−1: 3436 (NH), 3052 (Ar—H), 2953 (Alph-H), 1702 (C═O), 1614, 1515, 1425 (C═C), 1229 (C—N), 1162 (C—O). 1H NMR (500 MHz, DMSO-d6) δ=2.76 (m, 4H, 2CH2), 3.18 (m, 4H, 2CH2), 3.67 (s, 2H, CH2), 4.49 (s, 2H, CH2), 6.60 (d, 1H, J=2.3 Hz, aromatic H), 6.70 (dd, 1H, J=2.2, 8.5 Hz, aromatic H), 7.43-7.48 (m, 6H, aromatic H), 7.58-7.62 (m, 4H, aromatic H). 13C NMR (125.7 MHz, DMSO-d6) δ=43.70 (CH2), 48.23 (CH2), 53.03 (CH2), 62.64 (CH2), 114.56 (aromatic-C), 117.64 (aromatic-C), 119.82 (aromatic-C), 124.58 (aromatic-C), 127.19 (aromatic-C), 127.26 (aromatic-C), 127.55 (aromatic-C), 127.90 (aromatic-C), 128.95 (aromatic-C), 129.26 (aromatic-C), 130.25 (aromatic-C), 130.59 (aromatic-C), 136.66 (aromatic-C), 138.22 (aromatic-C), 138.66 (aromatic-C), 140.95 (aromatic-C), 146.88 (aromatic-C), 156.32 (C═O). Calculated (%) for C25H26N4O (398.21); C, 75.35; H, 6.58; N, 14.06. found (%); C, 75.27; H, 6.65; N, 13.96.

Workup

  1. stirringthe mixture was stirred for 6 h
  2. stirringstirred for 15 min
  3. customThe organic layer was separated
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. washColumn chromatography on silica gel, eluting with methanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-d87727c014c84ee2a028613ccee38d9b
Source dataset
uspto-grants-2015_12
Patent number
US09205087B1

Reaction notes

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