1-Hydroxybenzotriazole → 1-Acetyl-piperidine-4-carboxylic acid {3-[5-(2-bromo-3-methyl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propyl}-(3-chloro-4-methyl-phenyl)-amide

HRID 1374473Notes

Reaction equation

HRID 1374473 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.N=C=N.C1C=CC2N(O)N=NC=2C=1.[Cl:25][C:26]1[CH:27]=[C:28]([N:33]([CH2:45][CH2:46][CH2:47][N:48]2[CH2:55][CH:54]3[CH:50]([CH2:51][NH:52][CH2:53]3)[CH2:49]2)[C:34]([CH:36]2[CH2:41][CH2:40][N:39]([C:42](=[O:44])[CH3:43])[CH2:38][CH2:37]2)=[O:35])[CH:29]=[CH:30][C:31]=1[CH3:32].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:52]1[CH2:53][CH:54]2[CH2:55][N:48]([CH2:47][CH2:46][CH2:45][N:33]([C:28]3[CH:29]=[CH:30][C:31]([CH3:32])=[C:26]([Cl:25])[CH:27]=3)[C:34]([CH:36]3[CH2:37][CH2:38][N:39]([C:42](=[O:44])[CH3:43])[CH2:40][CH2:41]3)=[O:35])[CH2:49][CH:50]2[CH2:51]1)=[O:6]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 160435CarbodiimideHCID 27355882-Bromo-3-methylbenzoic acidHCID 58782555HCID 58782555, compound

Product 1

HCID 587825071-Acetyl-piperidine-4-carboxylic acid {3-[5-(2-bromo-3-methyl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propyl}-(3-chloro-4-methyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-bromo-3-methyl-benzoic acid (62, 0.016 g, 0.075 mmol), resin-bound carbodiimide (0.078 g, 0.15 mmol) and HOBT (0.012 g, 0.085 mmol) in DCM:DMF (1 mL, 10:1) was shaken for 18 h. A solution of 42b (0.022 g, 0.05 mmol) and DIPEA (0.03 mL, 0.17 mmol) and DCM (1 mL) was added. Shaking was continued for 24 h, the resin filtered and washed with DMF (1 mL) and twice with DCM (1 mL). The reaction mixture was concentrated in vacuo and purified by reverse phase HPLC to afford II-244: ms (ES+) m/z 644 (M+H)+.

Workup

  1. filtrationthe resin filtered
  2. washwashed with DMF (1 mL) and twice with DCM (1 mL)
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by reverse phase HPLC
  5. customto afford II-244: ms (ES+) m/z 644 (M+H)+

Sources & evidence

ORD record
ord-c9f3ebe400634f259c47786e38d4f34b
Source dataset
uspto-grants-2007_01
Patent number
US07164019B2

Reaction notes

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