Hydrochloric Acid → HCID 59285266, compound

HRID 906413Notes

Reaction equation

HRID 906413 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[C:18](=[O:22])[N:17]([CH2:23][CH2:24][CH2:25][OH:26])[CH:16]=[C:15]4[CH:27]=O)[C:9]([CH3:29])=[C:8]([F:30])[CH:7]=2)[CH2:3][CH2:2]1.C([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)(OC(C)(C)C)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCCl.O1CCOCC1.C(O)(=O)C>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[C:18](=[O:22])[N:17]([CH2:23][CH2:24][CH2:25][OH:26])[CH:16]=[C:15]4[CH2:27][N:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[C:9]([CH3:29])=[C:8]([F:30])[CH:7]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86640966HCID 86640966, compound

Product 1

HCID 59285266HCID 59285266, compoundYield 27.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Cyclopropyl-3-fluoro-5-(4-formyl-2-(3-hydroxypropyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide (Example 10e, 0.34 g) and 1-Boc-piperazine (0.30 g) were stirred together in DCE (10 ml) the overall pH of the reaction was adjusted to pH 6 by dropwise addition of glacial acetic acid. The mixture was stirred for 24 h, sodium triacetoxyborohydride (0.51 g) was added, and the resulting mixture was stirred at room temperature for 24 h. A solution of HCl in dioxan (5 mL of 4M) was added and the reaction mixture stirred for 2 h, evaporated to dryness and the residue purified by reverse phase preparative HPLC (Phenomenex column using a gradient of aqueous 0.2% ammonia in acetonitrile as eluent) to give the title compound (0.11 g).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 24 h
  2. stirringthe reaction mixture stirred for 2 h
  3. customevaporated to dryness
  4. customthe residue purified by reverse phase preparative HPLC (Phenomenex column

Sources & evidence

ORD record
ord-59914b2145354ce5a5f371cf8327ee54
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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