p-Toluenesulfonic acid monohydrate → HCID 86656588, compound

HRID 455990Notes

Reaction equation

HRID 455990 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:36])=[C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:25]4[C:20](=[C:21]([F:31])[CH:22]=[CH:23][C:24]=4[O:26][C:27]([F:30])([F:29])[F:28])[N:19]([CH2:32][CH2:33][O:34][CH3:35])[CH:18]=3)=[O:16])[CH2:11][CH2:10]2)[CH:8]=1.O.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(#N)C>[C:38]1([CH3:48])[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1.[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:36])=[C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:25]4[C:20](=[C:21]([F:31])[CH:22]=[CH:23][C:24]=4[O:26][C:27]([F:30])([F:28])[F:29])[N:19]([CH2:32][CH2:33][O:34][CH3:35])[CH:18]=3)=[O:16])[CH2:11][CH2:10]2)[CH:8]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 44631896[4-(5-aminomethyl-2-fluorophenyl)piperidine-1-yl][7-fluoro-1-(2-methoxyethyl)-4-trifluoromethoxy-1H-indol-3-yl]methanone

Product 1

HCID 86656588HCID 86656588, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of [4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1H-indol-3-yl]-methanone (488 mg, 0.95 mmol) in acetonitrile (3 mL) is added a solution of p-toluenesulfonic acid monohydrate (181 mg, 0.95 mmol) in acetonitrile (3 mL). This mixture is stored in a freezer overnight. The resulting beige crystal is collected by suction filtration, washed with toluene, and dried in vacuo at 50° C. overnight. The yield is 453 mg (69%). 1H NMR (DMSO-d6) δ 8.08 (bs, 3H), 7.70 (s, 1H), 7.80-6.95 (m, 9H), 5.00-4.30 (m, 3H), 4.20-3.90 (m, 2H), 3.80-3.60 (m, 3H), 3.23 (s, 3H), 3.25-2.80 (m, 3H), 2.28 (s, 3H), 1.95-1.45 (m, 4H); 19F NMR (DMSO-d6) δ −55.61 (s, 3F), −118.98 (s, 1F), −134.33 (d, J=9.3 Hz, 1F); LC 2.627 min; MS 512 (M+1, 100%). Mp 219° C. Infrared spectral features (cm−1): 1583, 1548, 1511, 1501, 1250, 1200, 1169, 1123, 1115.

Workup

  1. filtrationThe resulting beige crystal is collected by suction filtration
  2. washwashed with toluene
  3. customdried in vacuo at 50° C. overnight
  4. customLC 2.627 min

Sources & evidence

ORD record
ord-ecaf1ca221fb423fb3a518a3221bef2c
Source dataset
uspto-grants-2013_07
Patent number
US08497379B2

Reaction notes

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