Triethylamine → HCID 86664069, compound

HRID 1424644Notes

Reaction equation

HRID 1424644 reaction equation
[C:1]([O:5][C:6]([N:8]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:9]1[N:14]=[C:13]([CH2:15][C@@H:16]2[C@H:20]([O:21][CH2:22][CH:23]=O)[CH2:19][N:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17]2)[CH:12]=[C:11]([CH3:32])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH2:47][NH2:48].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[C:9]1[N:14]=[C:13]([CH2:15][C@@H:16]2[C@H:20]([O:21][CH2:22][CH2:23][NH:48][CH2:47][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[F:40])[CH2:19][N:18]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:17]2)[CH:12]=[C:11]([CH3:32])[CH:10]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666492-FluorobenzylamineHCID 86664070HCID 86664070, compound

Product 1

HCID 86664069HCID 86664069, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aldehyde 6 (100 mg, 0.18 mmol) in DCM (4 mL) was added (2-fluorophenyl)methanamine (45 mg, 0.36 mmol), triethylamine (11 μL, 0.36 mmol), followed by NaHB(OAc)3 (100 mg, 0.45 mmol). The reaction mixture was stirred for an additional 3 hand then concentrated. The crude product was purified by flash column chromatography (EtOAc/hexanes, 1:1, Rf=0.15) to yield 7a (115 mg, 91%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 1.43-1.44 (s, 27H), 2.29-2.30 (m, 3H), 2.60-2.75 (m, 1H), 2.76-2.85 (m, 2H), 2.92-3.00 (m, 1H), 3.05-3.14 (m, 1H), 3.20-3.50 (m, 5H), 3.52-3.70 (m, 2H), 3.72-3.80 (m, 1H), 3.91 (s, 2H), 6.84-6.85 (d, J=8.0 Hz, 1H), 6.89-6.91 (d, J=10.0 Hz, 1H), 7.02-7.06 (dd, J=9.0, 9.5 Hz, 1H), 7.10-7.13 (dd, J=7.0, 7.5 Hz, 1H), 7.20-7.30 (m, 1H), 7.35-7.40 (m, 1H); 13C NMR (125 MHz, CDCl3) δ 20.9, 24.7, 27.9, 28.47, 28.50, 29.7, 34.6, 34.7, 36.6, 42.6, 43.3, 46.8, 48.2, 48.8, 49.1, 50.3, 50.8, 68.0, 68.2, 78.7, 79.2, 79.3, 79.4, 82.8, 115.2, 115.3, 115.4, 115.5, 119.5, 119.6, 122.8, 124.17, 124.19, 128.89, 128.92, 128.95, 128.99, 130.46, 130.51, 130.55, 149.6, 151.4, 151.5, 151.8, 154.5, 154.8, 159.08, 159.14, 160.3, 162.2; LC-TOF (M+H+) calcd for C35H52FN4O7 659.3820. found 659.3818.

Workup

  1. concentrationthen concentrated
  2. customThe crude product was purified by flash column chromatography (EtOAc/hexanes, 1:1, Rf=0.15)

Sources & evidence

ORD record
ord-afecff57dad24964936e08ac3344483c
Source dataset
uspto-grants-2015_01
Patent number
US08927730B2

Reaction notes

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