3-Aminoazetidine, 3-BOC protected → HCID 57937324, compound

HRID 1435456Notes

Reaction equation

HRID 1435456 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].[NH:25]1[CH2:28][CH:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:26]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:25]3[CH2:28][CH:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937324HCID 57937324, compoundYield 83%

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 (0.74 g, 2.0 mmol), tert-butyl azetidin-3-ylcarbamate (0.35 g, 2.0 mmol) and DMAP (0.75 g, 6.1 mmol) in MeCN (60 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 0.84 g (83%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.32 (s, 9 H), 1.49-1.64 (m, 4 H), 1.66 (s, 9 H), 2.29-2.45 (m, 1 H), 3.30-3.41 (m, 2 H), 3.63 (m, 2 H), 3.88-4.01 (m, 4 H), 4.03-4.14 (m, 1 H), 4.52 (d, J=7.62 Hz, 2 H), 7.90 (dd, J=8.59, 1.37 Hz, 1 H), 8.05 (d, J=8.79 Hz, 1 H), 8.15 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=506.8; Anal. Calcd for C25H38N4O5S+0.90 TFA+0.10 EtOAc+0.50H2O (628.31): C, 52.19; H, 6.53; N, 8.92. Found: C, 52.13; H, 6.53; N, 8.84.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-f93f26e6bd8b4655a2deaa9173a93256
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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