Methanesulfonyl chloride → HCID 11642491, compound

HRID 1986630Notes

Reaction equation

HRID 1986630 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]([CH2:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=3)=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:23][C:18]1[CH:17]=[C:16]([NH:15][C:13](=[O:14])[N:12]([CH:8]2[CH2:9][C:10]3[CH:11]=[C:2]([NH:1][S:35]([CH3:34])(=[O:37])=[O:36])[CH:3]=[CH:4][C:5]=3[CH2:6][CH2:7]2)[CH2:24][CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]2)[CH:21]=[CH:20][C:19]=1[F:22]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 44417989HCID 44417989, compound

Product 1

HCID 11642491HCID 11642491, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-(3-chloro-4-fluoro-phenyl)-1-[3-(4-methyl-piperazin-1-yl)-propyl]-urea (from Preparative Example 27, 0.035 g, 0.074 mmol) in CH2Cl2 (0.2 mL) at 0° C. were added methanesulfonyl chloride (0.0058 mL, 0.074 mmol) and DIEA (0.039 mL, 0.22 mmol). The mixture was stirred from 0° C. to room temperature for 3 hours, then concentrated in vacuo, and the residue was purified by preparative HPLC to give 0.035 g (88%) of N-(7-{3-(3-chloro-4-fluoro-phenyl)-1-[3-(4-methyl-piperazin-1-yl)-propyl]-ureido}-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanesulfonamide as a light yellow gum. 1H NMR (300 MHz, CD3OD): δ 7.59 (dd, 1H, J=6.6, 2.7 Hz), 7.30 (ddd, 1H, J=9.0, 4.2, 2.7 Hz), 7.14 (t, 1H, J=9.0 Hz), 7.08 (d, 1H, J=8.4 Hz), 7.04-6.98 (m, 2H), 4.30 (m, 1H), 3.66 (m, 8H), 3.46 (m, 2H), 2.99 (m, 6H), 2.90 (s, 3H), 2.11 (m, 4H). MS-ESI: 552.0 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-486f668d05a84433ba6e898f7ed8d5a5
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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