Triethylamine → HCID 54675117, compound

HRID 2402755Notes

Reaction equation

HRID 2402755 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C@@H:11]2[C@@H:18]3[C@@H:14]([CH2:15][NH:16][CH2:17]3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=1.C(N(CC)CC)C>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C@@H:11]2[C@@H:18]3[C@@H:14]([CH2:15][N:16]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=4)[CH2:17]3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27829022-Bromo-6-(trifluoromethyl)pyridineHCID 54674971HCID 54674971, compound

Product 1

HCID 54675117HCID 54675117, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared by combining (3aS,4S,6aS)—N-(3-fluorophenyl)octahydrocyclopenta[c]pyrrole-4-carboxamide (98 mg, 0.395 mmol) from Example 55, 2-bromo-6-(trifluoromethyl)pyridine (125 mg, 0.553 mmol), and triethylamine (0.165 mL, 1.184 mmol) in ethanol (0.2 mL). The reaction mixture was heated at 80° C. for 72 hours. The reaction was quenched with water (1 mL) and the resulting brown oil was purified using a 12 g silica gel cartridge eluting with 1-100% ethyl acetate/hexanes over 20 minutes to give a solid. The solid was recrystallized from ethyl acetate/heptane (10%) to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 11.06 (s, 1H), 8.21 (dt, J=11.7, 2.2, 1H), 7.60-7.59 (m, 1H), 7.54-7.47 (m, 1H), 7.30 (td, J=8.2, 6.8, 1H), 6.98 (d, J=7.3, 1H), 6.91 (tdd, J=8.6, 2.6, 0.6, 1H), 6.41 (d, J=8.6, 1H), 3.46 (dd, J=10.3, 7.6, 3H), 3.23-3.14 (m, 1H), 3.06 (dd, J=10.8, 5.7, 1H), 2.90-2.72 (m, 2H), 2.22-2.12 (m, 1H), 2.12-1.95 (m, 2H), 1.39 (dtd, J=10.4, 8.0, 5.4, 1H); MS (ESI+) m/z 394 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe reaction was quenched with water (1 mL)
  3. customthe resulting brown oil was purified
  4. washeluting with 1-100% ethyl acetate/hexanes over 20 minutes
  5. customto give a solid
  6. customThe solid was recrystallized from ethyl acetate/heptane (10%)

Sources & evidence

ORD record
ord-4003509e88784bfd896d78c3c0ce1728
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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