1,2-Dichloroethane → HCID 69299464, compound

HRID 2196506Notes

Reaction equation

HRID 2196506 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([NH:7][NH2:8])=[O:6].[C:13]([O:17][C:18]([NH:20][C@@H:21]([CH3:43])[C:22]([NH:24][CH2:25][C:26]1[S:30][CH:29]=[C:28]([N:31]2[C:35]([C:36](O)=[O:37])=[CH:34][C:33]([C:39]([F:42])([F:41])[F:40])=[N:32]2)[CH:27]=1)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(Cl)CCl>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([NH:7][NH:8][C:36]([C:35]1[N:31]([C:28]2[CH:27]=[C:26]([CH2:25][NH:24][C:22](=[O:23])[C@@H:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:16])([CH3:14])[CH3:15])[CH3:43])[S:30][CH:29]=2)[N:32]=[C:33]([C:39]([F:40])([F:42])[F:41])[CH:34]=1)=[O:37])=[O:6]

Participants

6

Reactant 3

HCID 111,2-Dichloroethane2×HCID 24051o-AnisohydrazideHCID 69298555(S)-1-(5-((2-(tert-butoxycarbonylamino)propanamido)methyl)thiophen-3-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 69299464HCID 69299464, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxybenzhydrazide (0.040 g, 0.238 mmol) and compound 7 (preparation described in scheme 2 example 1c, step 7) (0.11 g, 0.238 mmol) in dichloromethane (2 mL) under nitrogen was added EDC (0.046 g, 0.238 mmol) followed by DMAP (5.81 mg, 0.048 mmol). The reaction was left to stir for 16 hours at room temperature. Another portion of EDC (20 mg, 0.104 mmol) was added and the reaction continued for 4 hours. The solvent was then removed on the rotary evaporator and the crude purified by silica gel column chromatography with a Biotage 12M column and a gradient of 0-5% methanol in dichloromethane to give compound 16 as a yellow crust (73.7 mg, 51%). LRMS (ESI): calc. 610.2; found 511.2 (MH-Boc)+, 633.3 (MNa)+.

Workup

  1. waitThe reaction was left
  2. waitthe reaction continued for 4 hours
  3. customThe solvent was then removed on the rotary evaporator
  4. customthe crude purified by silica gel column chromatography with a Biotage 12M column

Sources & evidence

ORD record
ord-3be6066b3be546068e08e9123ac6a100
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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