Hydrochloric Acid → HCID 46899204, compound

HRID 602802Notes

Reaction equation

HRID 602802 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]([CH:27]2[CH2:39][C:30]3[NH:31][C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][C:37]=4[C:29]=3[CH2:28]2)([F:26])[C:12]2[O:16][C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)=[N:14][N:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-].C[N:43]1CCOCC1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]([CH:27]2[CH2:39][C:30]3[NH:31][C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][C:37]=4[C:29]=3[CH2:28]2)([F:26])[C:12]2[O:16][C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([NH2:43])=[O:23])=[CH:24][CH:25]=3)=[N:14][N:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 46899290HCID 46899290, compound

Product 1

HCID 46899204HCID 46899204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 63 mg (0.1 mmol) of (RS, SR) 4-{5-[(3-bromo-benzenesulfonyl)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid (example 113) in 0.5 mL of DMF was treated with 27 mg (0.511 mmol) of NH4Cl, 61 mg (0.6 mmol) of N-methylmorpholine, 3 mg (0.02 mmol) and of 1-hydroxybenzotriazole. The mixture was stirred for 15 at 0° C. and treated with 29 mg (0.15 mmol) of EDCI and stirred at RT for 10 hrs. A diluted aqueous solution of HCl was added and the mixture extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and the solvent evaporated to give 60 mg of (RS, SR) 4-{5-[(3-bromo-benzenesulfonyl)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,3,4]oxadiazol-2-yl}-benzamide as a brown solid, MS: 630 (MH+, 1Br).

Workup

  1. stirringstirred at RT for 10 hrs
  2. extractionthe mixture extracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-bc1bc6361b4443959a09ca6b9457783c
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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