Water → HCID 118021773, compound

HRID 518276Notes

Reaction equation

HRID 518276 reaction equation
Cl.[CH3:2][N:3]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH3:20])[CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:21].N(C(C)C)(C(C)C)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33].O>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:20][N:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:21])[N:3]([CH3:2])[CH:12]=2)[CH:14]=1)[S:32]([CH3:31])(=[O:34])=[O:33]

Participants

8

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 118021551HCID 118021551, compound

Product 1

HCID 118021773HCID 118021773, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the title compound of Example 32 (35 mg, 0.12 mmol) in anhydrous CH2Cl2 (0.3 mL), pyridine (0.1 mL) and NEtiPr2 (0.021 mL, 0.12 mmol) was added methanesulfonyl chloride (0.011 mL, 0.14 mmol). After 0.5-1 h, ice was added to the mixture followed by water and ethyl acetate. Extractive work up, washing with H2O, a 1:1 aqueous saturated KHSO4:H2O, and brine, and purification on silica gel eluting with 35-80% EA in hexane over 6 min and continuing 80% isocratic EA gave the title compound (22 mg, 0.06 mmol) as a cream solid in 54% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.00 (s, 3H), 3.30 (s, 3H), 3.58 (s, 3H), 7.40 (d, J=7.58 Hz, 1H), 7.45-7.61 (m, 6H), 7.71 (td, J=7.58, 1.26 Hz, 1H), 8.34 (dd, J=8.21, 1.14 Hz, 1H). LCMS (M+H)+ 343.

Workup

  1. additionice was added to the mixture
  2. washExtractive work up, washing with H2O
  3. customa 1:1 aqueous saturated KHSO4:H2O, and brine, and purification on silica gel eluting with 35-80% EA in hexane over 6 min

Sources & evidence

ORD record
ord-c91eba7ec25e4966aceabc33f26e3067
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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