Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 23659706, compound

HRID 1435425Notes

Reaction equation

HRID 1435425 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].Cl.[CH3:26][NH:27][O:28][CH3:29]>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:27]([O:28][CH3:29])[CH3:26])(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659706HCID 23659706, 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), N,O-dimethylhydroxylamine hydrochloride (43 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 22 mg (25% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.41-1.55 (m, 4 H), 1.57 (s, 9 H), 2.26-2.40 (m, 1 H), 2.72 (s, 3 H), 3.30-3.37 (m, 2 H), 3.76 (s, 3 H), 3.86-3.95 (m, 2 H), 4.38 (d, J=7.42 Hz, 2 H), 7.73 (dd, J=8.6, 1.6 Hz, 1 H), 7.78 (d, J=8.2 Hz, 1 H), 8.10 (d, J=0.98 Hz, 1 H); MS (ESI) (M+H)+=396.0; Anal. Calcd for C19H29N3O4S+0.30 EtOAc (421.96): C, 57.50; H, 7.50; N, 9.96. Found: C, 57.88; H, 7.48; N, 9.95

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-8a1fdd33f99c41f293e5ecfc6a6b1bde
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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