Triethylamine → HCID 53391254, compound

HRID 400393Notes

Reaction equation

HRID 400393 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:10]=[C:11]([N:15]=[C:16]=[O:17])[CH:12]=[CH:13][CH:14]=1.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([S:25]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([Cl:44])[CH:38]=2)[C:31]#[N:32])(=[O:27])=[O:26])[CH2:21][CH2:20]1>C(Cl)Cl>[NH2:18][CH:19]1[CH2:20][CH2:21][N:22]([S:25]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][C:37]2[CH:38]=[C:39]([Cl:44])[CH:40]=[C:41]([Cl:43])[CH:42]=2)[C:31]#[N:32])(=[O:27])=[O:26])[CH2:23][CH2:24]1.[C:31]([C:30]1[CH:33]=[CH:34][C:35]([O:36][C:37]2[CH:38]=[C:39]([Cl:44])[CH:40]=[C:41]([Cl:43])[CH:42]=2)=[C:28]([S:25]([N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:16]([NH:15][C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[CH:10]=3)=[O:17])[CH2:20][CH2:21]2)(=[O:27])=[O:26])[CH:29]=1)#[N:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1230643-Fluorophenyl isocyanateHCID 58442575HCID 58442575, compound

Product 2

HCID 53391254HCID 53391254, compoundHCID 58442575HCID 58442575, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile was prepared following the procedure of Example 1. The final product was prepared by the addition of triethyl amine (0.42 mL) followed by 3-fluorophenyl isocyanate to a solution of 3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile (102 mg) in methylene chloride (4.0 mL). After stirring for 3 hours, the starting material was consumed, as confirmed by TLC (50% EtOAc/hexanes). 4 mL of hexanes was added and the product collected by vacuum filtration and washed with 1N HCl. The desired product was obtained as a white powder (99 mg, 73.3%). 1H NMR (500 MHz, DMSO-d6) δ: 8.61 (s, 1H), 8.28 (d, J=2 Hz, 1H), 8.13 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.55 (t, J=2 Hz, 2H), 7.42 (m, 1H), 7.37 (d, J=2 Hz, 2H), 7.34 (d, J=9 Hz, 1H), 7.22 (m, 1H), 6.99 (m, 1H), 6.68 (m, 1H), 6.33 (d, J=8 Hz, 1H), 3.61 (m, 3H), 2.96 (m, 2H), 1.88 (m, 2H), 1.40 (m, 2H). MS (ESI+ ion, m/z): 564.

Workup

  1. customthe starting material was consumed
  2. addition4 mL of hexanes was added
  3. filtrationthe product collected by vacuum filtration
  4. washwashed with 1N HCl

Sources & evidence

ORD record
ord-c8cfade4d12244aa9ba595fdbbf89a05
Source dataset
uspto-grants-2014_06
Patent number
US08741894B2

Reaction notes

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