3,3-Difluoroazetidine → HCID 23660484, compound

HRID 1435457Notes

Reaction equation

HRID 1435457 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].[F:25][C:26]1([F:30])[CH2:29][NH:28][CH2:27]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]([N:28]3[CH2:29][C:26]([F:30])([F:25])[CH2:27]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 27582483,3-DifluoroazetidineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23660484HCID 23660484, compoundYield 66.3%

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 (90 mg, 0.24 mmol), 3,3-difluoroazetidine (45 mg, 0.49 mmol) and DMAP (59 mg, 0.49 mmol) in MeCN (10 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 68 mg (66%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.46-1.63 (m, 4 H), 1.65 (s, 9 H), 2.27-2.44 (m, 1 H), 3.30-3.39 (m, 2 H), 3.89-3.98 (m, 2 H), 4.20 (t, J=12.30 Hz, 4 H), 4.51 (d, J=7.62 Hz, 2 H), 7.93 (dd, J=8.69, 1.66 Hz, 1 H), 8.05 (d, J=8.79 Hz, 1 H), 8.19 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=427.8; Anal. Calcd for C20H27F2N3O3S+1.10 TFA+0.3 CH3CN (565.26): C, 48.45; H, 5.17; N, 8.18. Found: C, 48.42; H, 4.86; N, 8.20.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-0d5821c3d96443f58bc48c89f663eef4
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…