Acetic Acid → [3-Chloro-2-fluoro-5-(4-methyl-piperazin-1-ylmethyl)-benzyl]-carbamic acid tert-butyl ester

HRID 1527494Notes

Reaction equation

HRID 1527494 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=O)[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH2:15][N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86673866HCID 86673866, compound

Product 1

HCID 68284159[3-Chloro-2-fluoro-5-(4-methyl-piperazin-1-ylmethyl)-benzyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

was prepared according to Scheme C2 (step C) from (3-chloro-2-fluoro-5-formyl-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.59 mmol), 1-methylpiperazine (59 mg, 0.59 mmol), acetic acid (0.053 mL, 0.89 mmol) and sodium triacetoxyborohydride (313 mg, 1.5 mmol) in THF (8 mL). MS (LC-MS): 372.0 [M]+; tR (HPLC conditions c): 3.64 min.

Workup

  1. customwas prepared
  2. custom3.64 min.

Sources & evidence

ORD record
ord-d32e6a2f30964c799af5106b1770a07d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…