Acetic Acid → (3-Chloro-5-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-2-fluoro-benzyl)-carbamic acid tert-butyl ester

HRID 1527500Notes

Reaction equation

HRID 1527500 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]([CH3:26])[CH2:22][CH2:23][NH:24][CH3:25].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]([CH2:23][CH2:22][N:21]([CH3:26])[CH3:20])[CH3:25])[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 5049666Sodium triacetoxyborohydrideHCID 86673866HCID 86673866, compound

Product 1

HCID 68284327(3-Chloro-5-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-2-fluoro-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), N,N,N′-trimethyl-ethylendiamine (71 mg, 0.70 mmol), acetic acid (0.06 mL, 1.0 mmol) and sodium triacetoxyborohydride (368 mg, 1.7 mmol) in THF (8 mL). MS (LC-MS): 374.0 [M]+; tR (HPLC conditions c): 3.53 min.

Workup

  1. customwas prepared
  2. custom3.53 min.

Sources & evidence

ORD record
ord-55f631e6d5864b6d865af7b1e6905d47
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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