Ammonia → HCID 25020454, compound

HRID 907345Notes

Reaction equation

HRID 907345 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH:29]=O)[CH:7]=2)[CH2:3][CH2:2]1.[CH3:32][C@@H:33]1[NH:38][CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]1.C([BH3-])#N.[Na+].Cl.N>O1CCOCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(OCC)(=O)C.CO>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH2:29][N:38]3[CH2:37][CH2:36][NH:35][CH2:34][C@@H:33]3[CH3:32])[CH:7]=2)[CH2:3][CH2:2]1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 7023035(S)-1-Boc-3-methylpiperazineHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Product 1

HCID 25020454HCID 25020454, compound

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 75 step i) (200 mg), (S)-3-methyl-piperazine-1-carboxylic acid, tert-butyl ester (287 mg) and titanium(IV) isopropoxide (3 mL) were stirred at room temperature for 15 hours. Methanol (10 mL) was then added followed by sodium cyanoborohydride (90 mg) and the mixture stirred for 15 hours. Methanol (10 mL) was then added followed by 4M HCl in 1,4-dioxane (10 mL) and the mixture stirred overnight at room temperature. The mixture was then poured into aqueous dilute ammonia and ethyl acetate added. The organics were decanted and evaporated to dryness. The residue was purified by HPLC to give the title compound as a solid (40 mg).

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. additionadded
  3. customThe organics were decanted
  4. customevaporated to dryness
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9f6591df94bc4f91ad9b09f4036af1a1
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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