Aniline → HCID 23659490, compound

HRID 1435418Notes

Reaction equation

HRID 1435418 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].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6115AnilineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659490HCID 23659490, 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), aniline (46 uL, 47 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 (1:1) on silica gel to give 43 mg (50% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.40-1.58 (m, 4 H), 1.61 (s, 9 H), 2.21-2.38 (m, 1 H), 3.29-3.35 (m, 2 H), 3.85-3.93 (m, 2 H), 4.45 (d, J=7.62 Hz, 2 H), 6.96-7.04 (m, 1 H), 7.04-7.11 (m, 2 H), 7.11-7.21 (m, 2 H), 7.84-7.89 (m, 1 H), 7.91-7.98 (m, 1 H), 8.06 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=428.0; Anal. Calcd for C23H29N3O3S+1.10 TFA+0.30 EtOAc+0.2H2O (583.03): C, 54.39; H, 5.69; N, 7.21. Found: C, 54.43; H, 5.68; N, 7.22.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-1fbd5c52de874c10854d9f9af0a2c448
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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