(2-Benzyloxy-phenyl)-methanesulfonyl chloride → methyl 4-{3-[2-[2-({[2-(benzyloxy)benzyl]sulfonyl}amino)ethyl]-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoate

HRID 225994Notes

Reaction equation

HRID 225994 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[CH:10][C:9]([Cl:26])=[CH:8][CH:7]=2.[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH2:54][S:55](Cl)(=[O:57])=[O:56])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH2:54][S:55]([NH:1][CH2:2][CH2:3][C:4]1[N:5]([CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[CH:10][C:9]([Cl:26])=[CH:8][CH:7]=2)(=[O:56])=[O:57])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

3

Reactant 2

HCID 11347020(2-Benzyloxy-phenyl)-methanesulfonyl chlorideHCID 21962240methyl 4-{3-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]propyl}benzoate

Product 1

HCID 68428312methyl 4-{3-[2-[2-({[2-(benzyloxy)benzyl]sulfonyl}amino)ethyl]-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoateYield 70.4%

Procedure

As outlined in Step 9 Example 1, methyl 4-{3-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]propyl}benzoate (Example 7, Step 6, 3.92 g, 7.3 mmol) was reacted with (2-benzyloxy-phenyl)-methanesulfonyl chloride (2.6 g, 8.76 mmol) to afford 4.1 g of methyl 4-{3-[2-[2-({[2-(benzyloxy)benzyl]sulfonyl}amino)ethyl]-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoate, a white foam, in 59% yield. 1H NMR (400 MHz, CDCl3) δ 1.80-1.99 (m, 2 H) 2.49-2.78 (m, 6 H) 2.85 (t, J=8.84 Hz, 2 H) 3.89 (s, 3 H) 3.96-4.05 (m, 1 H) 4.26 (s, 2 H) 4.90 (s, 2 H) 6.45 (d, J=8.84 Hz, 1 H) 6.73-6.82 (m, 2 H) 6.83-6.93 (m, 2 H) 6.94-7.08 (m, 4 H) 7.16-7.34 (m, 15 H) 7.39 (d, J=2.02 Hz, 1 H) 7.85-7.98 (m, 2 H).

Sources & evidence

ORD record
ord-99e964ccccfa4d6686315bb7030a43ae
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

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