Toluene → HCID 136347245, compound

HRID 601321Notes

Reaction equation

HRID 601321 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].CS[C:18](SC)=[C:19]1[C:28](=[O:29])[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:30][CH2:31][CH2:32][CH3:33])[C:20]1=[O:34].[C:37]1(C)C=CC=CC=1>>[OH:29][C:28]1[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:30][CH2:31][CH:32]([CH3:37])[CH3:33])[C:20](=[O:34])[C:19]=1[C:18]1[NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=2[S:7](=[O:8])(=[O:9])[N:10]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 10314079HCID 10314079, compoundHCID 574551872-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

Product 1

HCID 136347245HCID 136347245, compoundYield 49%

Procedure

The product of Example 309G (37.5 mg, 0.15 mmol) and the product of Example 340D (50 mg, 0.15 mmol) were reacted in toluene (5 mL) at 100° C. for 3 hours. The reaction was concentrated under reduced pressure and the residue was purified by chromatography on silica gel using a Biotage-12 m column eluting with 2:98 methanol:dichloromethane to give the title compound as a yellow solid (36 mg, 49%). The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) δ 0.98 (d, J=6.99 Hz, 6 H), 1.57 (m, 2 H), 1.66 (m, 1 H), 4.45 (d, J=7.35 Hz, 2 H), 4.64 (s, 3 H), 4.71 (s, 3 H), 7.43 (s, 1 H), 7.46 (m, 1 H), 8.54 (d, J=6.99 Hz, 1 H), 8.87 (s, 1 H), 14.45 (br.s, 1 H). MS (DCI+) m/z 510 (M+NH4)+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel using a Biotage-12 m column
  3. washeluting with 2:98 methanol

Sources & evidence

ORD record
ord-3f38e230f04746e7906f4a0ad04a2cfe
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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