Chloroacetyl chloride → HCID 70981529, compound

HRID 1475523Notes

Reaction equation

HRID 1475523 reaction equation
[CH2:1]([C:8]1[N:13]=[CH:12][C:11]2[C:14]([CH3:18])([CH3:17])[CH2:15][NH:16][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:20][C:21](Cl)=[O:22].C(O)(=O)C.C(O)(=O)C.[F:32][CH2:33][CH:34]1[CH2:39][NH:38][CH2:37][CH2:36][NH:35]1>>[CH2:1]([C:8]1[N:13]=[CH:12][C:11]2[C:14]([CH3:18])([CH3:17])[CH2:15][N:16]([C:21](=[O:22])[CH2:20][N:38]3[CH2:37][CH2:36][NH:35][CH:34]([CH2:33][F:32])[CH2:39]3)[C:10]=2[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 70980189HCID 70980189, compoundHCID 131732780HCID 131732780, compound

Product 1

HCID 70981529HCID 70981529, compound

Procedure

Prepared in an analogous method to that described in Prep 203 using 6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine, chloroacetyl chloride and 2-fluoromethyl-piperazine, diacetate salt. The product was purified by preparative HPLC (basic method) to provide the title compound (0.05 g). 1H NMR (Me-d3-OD): 8.24 (1H, s), 7.93 (1H, s), 7.36-7.14 (5H, m), 4.53-4.39 (1H, m), 4.39-4.26 (1H, m), 4.10 (2H, s), 4.05-3.66 (3H, m), 3.52-3.37 (2H, m), 3.25-2.76 (5H, m), 2.31 (1H, d), 2.25-2.08 (1H, m), 1.42 (6H, s). MS: [M+H]+=397.

Workup

  1. customPrepared in an analogous method to
  2. customThe product was purified by preparative HPLC (basic method)

Sources & evidence

ORD record
ord-69e2a6b049794204b91abadb22396d3e
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…