Hydrochloric Acid → HCID 68514769, compound

HRID 1716315Notes

Reaction equation

HRID 1716315 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]([C@H:7]([C:31]([O:33]C)=[O:32])[CH2:8][N:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[S:10]([CH3:13])(=[O:12])=[O:11])[CH3:6].Cl.CCCCCC>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]([C@H:7]([C:31]([OH:33])=[O:32])[CH2:8][N:9]([C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=2)=[CH:18][CH:19]=1)[S:10]([CH3:13])(=[O:11])=[O:12])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 68512753HCID 68512753, compound

Product 1

HCID 68514769HCID 68514769, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-{(2S)-2-[N-(3-Chloropropyl)-N-methylamino]-2-methoxy-carbonylethyl}-N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (350 mg, 0.67 mmol) from Step D in THF (1.5 mL) was added lithium hydroxyl (1.0 M in H2O, 1.34 mL, 1.34 mmol) at room temperature. The mixture was stirred at rt for 3 h. Then, HCl(aq) (2 N, 0.67 mL, 0.67 mmol) and hexane (15 mL) were added sequentially. The resulting solid was filtered and was washed with H2O (50 mL) and hexane (100 mL). The solid was then dried to give 317 mg of the titled compound (92%) as a pale brown solid. 1H NMR (300 MHz, d6-DMSO) δ 12.60 (br s, 1H), 7.76 (d, J=9.0 Hz, 2H), 7.46 (d, J=9.0 Hz, 2H), 7.19 (d, J=9.0 Hz, 2H), 7.16 (d, J=9.0 Hz, 2H), 3.96-3.80 (m, 2H), 3.59 (t, J=9.0 Hz, 2H), 3.20 (t, J=7.5 Hz, 1H), 3.00 (s, 3H), 2.67-2.46 (m, 2H), 2.20 (s, 3H), 1.82-1.70 (m, 2H); MS (EI) 509 (M++1), 507 (M+−1, 100).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwas washed with H2O (50 mL) and hexane (100 mL)
  3. customThe solid was then dried

Sources & evidence

ORD record
ord-8bdbef202b1640998e51019a0946e04e
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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