HCID 68543069, compound → HCID 68542292, compound

HRID 1446758Notes

Reaction equation

HRID 1446758 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:29])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:23]4[CH:24]=[CH:25][C:26](Cl)=[CH:27][C:22]4=[N:21][CH:20]=3)=[CH:15][CH:14]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)[NH:36][CH2:37][CH2:38][S:39]([C:42]1[CH:47]=[CH:46][C:45](B2OC(C)(C)C(C)(C)O2)=[CH:44][CH:43]=1)(=[O:41])=[O:40])(C)(C)C>>[NH2:36][CH2:37][CH2:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:26]2[CH:25]=[CH:24][N:23]3[C:19]([C:16]4[CH:17]=[CH:18][C:13]([CH2:12][C:11]([NH:10][C:7]5[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[O:9][N:8]=5)=[O:29])=[CH:14][CH:15]=4)=[CH:20][N:21]=[C:22]3[CH:27]=2)=[CH:44][CH:43]=1)(=[O:41])=[O:40]

Participants

3

Reactant 2

HCID 68543069HCID 68543069, compoundHCID 68545331HCID 68545331, compound

Product 1

HCID 68542292HCID 68542292, compoundYield 80.7%

Procedure

Couple N-(5-tert-Butyl-isoxazol-3-yl)-2-[4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetamide (0.700 g, 1.71 mmol) to {2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonyl]-ethyl}-carbamic acid tert-butyl ester (0.775 g, 1.88 mmol) using procedure similar to Example 115. Treat the crude extracts to SCX ion exchange chromatography during which time some of the BOC-group is cleaved. Elute from the SCX column and treat with 2N HCl in dioxane (125 mL) and 10 mL of methanol for 2 hours. Evaporate in vacuo to provide the intermediate (0.87 g, 1.38 mmol). MS(ES), m/z 616 (M+1).

Workup

  1. washElute from the SCX column
  2. additiontreat with 2N HCl in dioxane (125 mL) and 10 mL of methanol for 2 hours
  3. customEvaporate in vacuo

Sources & evidence

ORD record
ord-9fe67f68fddd4e79a2431a8c63c043b4
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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