Tert-Butylamine → HCID 23659704, compound

HRID 1435423Notes

Reaction equation

HRID 1435423 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].[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26]>CN(C1C=CN=CC=1)C.CC#N>[C:25]([NH:29][S:21]([C:19]1[CH:18]=[CH:17][C:8]2[N:9]([CH2:10][CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][C:7]=2[CH:20]=1)(=[O:23])=[O:22])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659704HCID 23659704, 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), tert-butylamine (32 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 40 mg (41% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.17 (s, 9 H), 1.49-1.64 (m, 4 H), 1.66 (s, 9 H), 2.29-2.44 (m, 1 H), 3.29-3.38 (m, 2 H), 3.87-3.97 (m, 2 H), 4.52 (d, J=7.62 Hz, 2 H), 7.97-8.05 (m, 2 H), 8.21 (dd, J=1.46, 0.68 Hz, 1 H); MS (ESI) (M+H)+=408.0; Anal. Calcd for C21H33N3O3S+1.200 TFA+0.20 EtOAc+0.1H2O (563.83): C, 51.55; H, 6.44; N, 7.45. Found: C, 51.59; H, 6.28; N, 7.41.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-494f7e4bf1b94aafa45418122ca2077d
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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