Methanesulfonyl chloride → HCID 11626998, compound

HRID 2102376Notes

Reaction equation

HRID 2102376 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=4)[NH2:25])=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(C(C)C)CC)(C)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[C:24]([NH:25][S:30]([CH3:29])(=[O:32])=[O:31])[CH:26]=[CH:27][CH:28]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11646895HCID 11646895, compound

Product 1

HCID 11626998HCID 11626998, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)aniline (50 mg, 0.126 mmol) in dichloromethane (1.5 mL) was added to methanesulfonyl chloride (58 mg, 0.51 mmol) while stirring, followed by the addition of a solution of diisopropylethylamine (18 mg, 0.14 mmol) in dichloromethane (0.5 mL). Stirring was continued for 12 hours at room temperature and then the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate (30 mL), washed with sodium bicarbonate (2×25 mL) and the organic layer was isolated and concentrated. The product was purified by silica gel chromatography using 40% ethyl acetate in hexanes to give 23 mg (40%) of N-[3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)phenyl]methanesulfonamide as a yellow solid. MS [M+H] 474.7. 1H NMR (400 MHz, CDCl3) δ (ppm) 8.65 (s, 1H), 7.42 (m, 2H), 7.23 (t, J=68.0 Hz, 1H), 7.22 (s, 1H), 7.06-7.01 (m, 2H), 6.76 (dd, J=8.0, 2.0 Hz, 1H), 6.68 (t, J=2.4 Hz, 1H), 6.58 (dd, J=8.0, 2.4 Hz, 1H), 6.32 (b, 1H), 4.58 (t, J=6.0 Hz, 2H), 3.01 (s, 3H), 2.07 (m, 2H).

Workup

  1. stirringStirring
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  4. washwashed with sodium bicarbonate (2×25 mL)
  5. customthe organic layer was isolated
  6. concentrationconcentrated
  7. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-850d43401fc141dba9d0a2a78d768631
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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