Ammonia → 7-methoxy-3-{1-[6-(7-methyl-1H-indazole-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469404Notes

Reaction equation

HRID 469404 reaction equation
[CH3:1][O:2][C:3]1[CH:46]=[CH:45][C:6]2[NH:7][C:8](=[O:44])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([C:24]([C:26]5[CH:27]=[C:28]6[C:32](=[C:33]([CH3:35])[CH:34]=5)[N:31](COCC[Si](C)(C)C)[N:30]=[CH:29]6)=[O:25])[N:21]=[CH:20][N:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl.N.O>CO.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:46]=[CH:45][C:6]2[NH:7][C:8](=[O:44])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([C:24]([C:26]5[CH:27]=[C:28]6[C:32](=[C:33]([CH3:35])[CH:34]=5)[NH:31][N:30]=[CH:29]6)=[O:25])[N:21]=[CH:20][N:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 581812007-methoxy-3-(1-{6-[7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-5-carbonyl]-pyrimidin-4-yl}-piperidin-4-yl)-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Product 1

HCID 252704757-methoxy-3-{1-[6-(7-methyl-1H-indazole-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

65 mg (0.10 mmol) 7-methoxy-3-(1-{6-[7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-5-carbonyl]-pyrimidin-4-yl}-piperidin-4-yl)-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one in 0.4 mL MeOH and 0.6 mL (2.4 mmol) of a 4 molar HCl solution in dioxane was stirred overnight at RT. The mixture was neutralised with 0.4 mL of a 6 molar methanolic ammonia solution, mixed with some water and purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. custompurified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customfreeze-dried

Sources & evidence

ORD record
ord-3281b5d8b31f404e9a65608d79db0e2f
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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