Succinic Acid → HCID 86624188, compound

HRID 1191154Notes

Reaction equation

HRID 1191154 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]([NH:26][C:27]([CH:29]3[CH2:31][CH2:30]3)=[O:28])[S:24][CH:25]=2)=[CH:17][CH:16]=1.ClCCl.[C:35]([OH:42])(=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39]>C(O)C>[C:35]([OH:42])(=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39].[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:22]=[C:23]([NH:26][C:27]([CH:29]3[CH2:31][CH2:30]3)=[O:28])[S:24][CH:25]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1110Succinic AcidHCID 6344DichloromethaneHCID 59828868HCID 59828868, compound

Product 1

HCID 86624188HCID 86624188, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 7-chloro-6-{4-[2-(cyclopropanecarbonyl-amino)-thiazol-4-yl]-benzylamino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.136 g, 0.3 mmol) in absolute ethanol (5 mL) at room temperature, add dichloromethane (5 mL). Add succinic acid (0.035 g, 0.301 mmol) to the mixture and stir for 1 h. Concentrate in vacuo. Combine the residue with MTBE (5 mL) and concentrate three times to afford a white solid. Dry the white solid in a vacuum oven at 40° C. overnight to afford the title compound (160 mg, 93%) as a white solid. MS (ES+) m/z: 453 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. concentrationconcentrate three times
  3. customto afford a white solid
  4. customDry the white solid in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-6587c236dfa5479ba41027e06c2c6904
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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