Thiophenol → HCID 58972606, compound

HRID 1485364Notes

Reaction equation

HRID 1485364 reaction equation
[CH3:1][S:2]([C:5]1[N:6]=[C:7]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[C:8]2[CH2:14][CH2:13][N:12]([C:15]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:10][C:9]=2[N:25]=1)(=O)=O.[C:37]1(S)[CH:42]=[CH:41]C=[CH:39][CH:38]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[C:1]1([S:2][C:5]2[N:6]=[C:7]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[C:8]3[CH2:14][CH2:13][N:12]([C:15]4[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:11][CH2:10][C:9]=3[N:25]=2)[CH:41]=[CH:42][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 58972737HCID 58972737, compound

Product 1

HCID 58972606HCID 58972606, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave reaction vial were added [2-methanesulfonyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amine (53 mg, 0.1 mmol), thiophenol (16 mg, 0.15 mmol), p-toluenesulfonic acid monohydrate (10 mg, 0.05 mmol), and DMF (0.4 mL). The vial was capped, and the mixture was heated via microwave irradiation at 100° C. for 10 min, filtered through a 0.45 μm filter, and the filtrate was purified by reversed phase HPLC (Phenomenex Gemini 30 mm×100 mm column, gradient of acetonitrile in 20 mM aqueous NH4OH). The title compound was obtained as a white solid (27 mg, 48%). MS (ESI): mass calcd. for C27H21F6N5S, 561.14; m/z found, 562 [M+H]+. 1H NMR (CDCl3): 8.38 (dd, J=4.7, 1.5 Hz, 1H), 7.88 (dd, J=7.8, 1.8 Hz, 1H), 7.68-7.62 (m, 2H), 7.56-7.50 (m, 1H), 7.50-7.42 (m, 2H), 7.23 (d, J=8.7 Hz, 2H), 7.16 (d, J=8.7 Hz, 2H), 6.96 (dd, J=7.4, 4.6 Hz, 1H), 6.58 (bs, 1H), 3.66-3.55 (m, 4H), 3.23-3.17 (m, 2H), 2.96-2.90 (m, 2H).

Workup

  1. customTo a microwave reaction
  2. customThe vial was capped
  3. filtrationfiltered through a 0.45 μm
  4. filtrationfilter
  5. customthe filtrate was purified by reversed phase HPLC (Phenomenex Gemini 30 mm×100 mm column, gradient of acetonitrile in 20 mM aqueous NH4OH)

Sources & evidence

ORD record
ord-fae14bd10b534f199735caedfa4fbba9
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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