N-Methylcyclohexylamine → HCID 23659705, compound

HRID 1435424Notes

Reaction equation

HRID 1435424 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:25]1([NH:31][CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C.CC#N>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([N:31]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH3:32])(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659705HCID 23659705, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (82 mg, 0.22 mmol), cyclohexyl(methyl)amine (50 mg, 0.44 mmol) and DMAP (54 mg, 0.44 mmol) in MeCN (4 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 58 mg (59% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.22-1.32 (m, 2 H), 1.33-1.44 (m, 4 H), 1.47-1.62 (m, 6 H), 1.65 (s, 9 H), 1.66-1.74 (m, 2 H), 2.27-2.44 (m, 1 H), 2.76 (s, 3 H), 3.29-3.38 (m, 2 H), 3.68-3.81 (m, 1 H), 3.87-3.97 (m, 2 H), 4.50 (d, J=7.42 Hz, 2 H), 7.89 (dd, J=8.79, 1.76 Hz, 1 H), 8.00 (d, J=8.79 Hz, 1 H), 8.12 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=448.0; Anal. Calcd for C24H37N3O3S+1.00 TFA+0.30 EtOAc+0.2H2O (591.70): C, 55.21; H, 6.95; N, 7.10. Found: C, 55.22; H, 6.85; N, 7.08.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-4b63749a73e9445786c04ab907de18ec
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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