Lithium borohydride → HCID 57947746, compound

HRID 340909Notes

Reaction equation

HRID 340909 reaction equation
[Cl:1][C:2]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:3]=1[CH2:4][NH:5][C:6](=[O:32])[N:7]([C@H:9]([CH2:17][O:18][C:19](=[O:31])[NH:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:11][CH2:12][C:13](OC)=[O:14])[CH3:8].[Li+].[BH4-]>CO.C1COCC1>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[C:21]([NH:20][C:19](=[O:31])[O:18][CH2:17][C@@H:9]([N:7]([CH3:8])[C:6]([NH:5][CH2:4][C:3]2[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:2]=2[Cl:1])=[O:32])[CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[N:22]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 57947475HCID 57947475, compound

Product 1

HCID 57947746HCID 57947746, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 5-(3-(2-chloro-4-fluorobenzyl)-1-methylureido)-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate (80 mg, 0.15 mmol) in MeOH (1 mL) and THF (1 mL) was added LiBH4 (2 M in THF, 0.3 mL, 4 equiv.) dropwise. The reaction was stirred at RT for 2 h. The reaction was quenched with saturated NH4Cl (5 mL). The mixture was extracted with EtOAc (10 mL). The organic layer was concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-2-(3-(2-chloro-4-fluorobenzyl)-1-methylureido)-6-hydroxyhexyl isoquinolin-3-ylcarbamate as a white solid 10 (40 mg, 53%). LRMS (M+H+) m/z 503.5.

Workup

  1. customThe reaction was quenched with saturated NH4Cl (5 mL)
  2. extractionThe mixture was extracted with EtOAc (10 mL)
  3. concentrationThe organic layer was concentrated
  4. customThe resulting residue was purified on RP-HPLC
  5. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-bce813e7661547ac8f4562c07ecc7976
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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