Chloroacetyl chloride → (2R,5R)-4-{2-[6-(2-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475450Notes

Reaction equation

HRID 1475450 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][OH:15])[NH:11][CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:18][C:19](Cl)=[O:20].[F:22][C:23]1[CH:40]=[CH:39][CH:38]=[CH:37][C:24]=1[CH2:25][C:26]1[N:31]=[CH:30][C:29]2[C:32]([CH3:36])([CH3:35])[CH2:33][NH:34][C:28]=2[CH:27]=1.CCN(C(C)C)C(C)C>C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][OH:15])[N:11]([CH2:18][C:19]([N:34]2[C:28]3[CH:27]=[C:26]([CH2:25][C:24]4[CH:37]=[CH:38][CH:39]=[CH:40][C:23]=4[F:22])[N:31]=[CH:30][C:29]=3[C:32]([CH3:36])([CH3:35])[CH2:33]2)=[O:20])[CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 709804176-(2-fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridineHCID 71003242(2R,5R)-tert-Butyl 5-(hydroxymethyl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 70980099(2R,5R)-4-{2-[6-(2-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Prepared from (2R,5R)-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester, chloroacetyl chloride and 6-(2-fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine using an analogous method to Preparation 203, but with DIPEA as base instead of triethylamine and heating carried out at 40° C. (See also General Procedure 5, below). MS: [M+H]+=527.

Workup

  1. customto Preparation 203
  2. customcarried out at 40° C.

Sources & evidence

ORD record
ord-68c391aab14e48b59b6ce872afe2479c
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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