N-Methylisobutylamine → HCID 23659703, compound

HRID 1435422Notes

Reaction equation

HRID 1435422 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].[CH2:25]([NH:29][CH3:30])[CH:26]([CH3:28])[CH3:27]>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:29]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH3:30])(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 12249N-MethylisobutylamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659703HCID 23659703, 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), isobutyl(methyl)amine (38 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 54 mg (58% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.91 (d, J=6.64 Hz, 6 H), 1.46-1.61 (m, 4 H), 1.64 (s, 9 H), 1.82-1.95 (m, 1 H), 2.25-2.45 (m, 1 H), 2.69 (s, 3 H), 2.74 (d, J=7.42 Hz, 2 H), 3.29-3.40 (m, 2 H), 3.87-4.00 (m, 2 H), 4.49 (d, J=7.42 Hz, 2 H), 7.82 (dd, J=8.69, 1.66 Hz, 1 H), 7.98 (d, J=8.79 Hz, 1 H), 8.08 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=422.0; Anal. Calcd for C22H35N3O3S+0.90 TFA+0.20 EtOAc (541.85): C, 54.53; H, 6.98; N, 7.75. Found: C, 54.53; H, 6.99; N, 7.77.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-bbe0bb3e61d545dd99381db7b0b4c890
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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