N,3-Dimethyl-1-butanamine → HCID 23659493, compound

HRID 1435421Notes

Reaction equation

HRID 1435421 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].[CH3:25][NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30]>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:26]([CH3:25])[CH2:27][CH2:28][CH:29]([CH3:31])[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 521020N,3-Dimethyl-1-butanamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659493HCID 23659493, 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), methyl (3-methylbutyl)amine (45 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 57 mg (60% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.89 (d, J=6.64 Hz, 6 H), 1.39 (q, J=6.90 Hz, 2 H), 1.46-1.61 (m, 5 H), 1.64 (s, 9 H), 2.26-2.43 (m, 1 H), 2.70 (s, 3 H), 2.97-3.06 (m, 2 H), 3.29-3.38 (m, 2 H), 3.86-3.97 (m, 2 H), 4.48 (d, J=7.42 Hz, 2 H), 7.81 (dd, J=8.79, 1.76 Hz, 1 H), 7.96 (d, J=8.79 Hz, 1 H), 8.07 (d, J=1.37 Hz, 1 H); MS (ESI) (M+H)+=436.0; Anal. Calcd for C23H37N3O3S+0.70 TFA+0.30 EtOAc+0.5H2O (550.89): C, 55.82; H, 7.52; N, 7.63. Found: C, 55.90; H, 7.46; N, 7.63.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-deb3422720ba41d7b2ac100db2702d08
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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