Morpholine → HCID 23659489, compound

HRID 1435417Notes

Reaction equation

HRID 1435417 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[CH2:30][CH2:29][O:28][CH2:27][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[CH2:30][CH2:29][O:28][CH2:27][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 8083MorpholineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659489HCID 23659489, 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), morpholine (44 uL, 44 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 (1:2) on silica gel to give 43 mg (50% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.47-1.62 (m, 4 H), 1.65 (s, 9 H), 2.28-2.43 (m, 1 H), 2.92-3.04 (m, 4 H), 3.29-3.40 (m, 2 H), 3.64-3.74 (m, 4 H), 3.88-3.98 (m, 2 H), 4.51 (d, J=7.42 Hz, 2 H), 7.83 (dd, J=8.79, 1.76 Hz, 1 H), 8.03 (d, J=8.79 Hz, 1 H), 8.08 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=422.0; Anal. Calcd for C21H31N3O4S+0.90 TFA+0.20 EtOAc+0.80H2O (556.22): C, 50.96; H, 6.36; N, 7.55. Found: C, 50.94; H, 6.46; N, 7.51.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-b7c56e1638894ff9b3c9caf683566660
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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