Cyclohexylamine → HCID 23659488, compound

HRID 1435416Notes

Reaction equation

HRID 1435416 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([NH2:31])[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]([NH:31][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659488HCID 23659488, 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 (76 mg, 0.20 mmol), cyclohexylamine (57 uL, 50 mg, 0.50 mmol) and DMAP (82 mg, 0.67 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 39 mg (44% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.09-1.23 (m, 6 H), 1.49-1.59 (m, 4 H), 1.58-1.66 (m, 4 H), 1.68 (s, 9 H), 2.31-2.46 (m, 1 H), 2.96-3.10 (m, 1 H), 3.31-3.40 (m, 2 H), 3.90-3.99 (m, 2 H), 4.53 (d, J=7.42 Hz, 2 H), 7.99 (dd, J=8.7, 1.7 Hz, 1 H), 8.05 (d, J=8.8 Hz, 1 H), 8.21 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=434.0; Anal. Calcd for C23H35N3O3S+1.10 TFA+0.40 EtOAc+0.3H2O (599.69): C, 53.68; H, 6.71; N, 7.01. Found: C, 53.61; H, 6.74; N, 7.02.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-eaf0b0a541f64a83847748151bc0e131
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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