Ammonia → HCID 19041650, compound

HRID 1684013

Reaction equation

HRID 1684013 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21](O)=[O:22])=[C:8]2[CH3:25])=[CH:4][CH:3]=1.C[N:29](C=O)C.C(Cl)(=O)C(Cl)=O.N>C1C=CC=CC=1.C1COCC1>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21]([NH2:29])=[O:22])=[C:8]2[CH3:25])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 98673334-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

Product 1

HCID 19041650HCID 19041650, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the acid of Example 7, Step 6, (600 mg, 1.39 mmol) in benzene (10.0 mL) was added at 0° C. DMF (50 mL) and oxalyl chloride. After a period of 30 min at 0° /C., THF (10.0 mL) was added to the resulting mixture and ammonia gas was bubbled until saturation. The mixture was stirred for 4 h at r.t. The reaction was poured over water, extracted with EtOAc, dried over Na2SO4, evaporated in vacuo and filtered over silica gel (50% EtOAc in THF) to provide the desired amide (530 mg).

Workup

  1. customwas bubbled until saturation
  2. additionThe reaction was poured over water
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. filtrationfiltered over silica gel (50% EtOAc in THF)

Sources & evidence

ORD record
ord-123036ca79af4ffc871ceb1d5ffa7a11
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Linked notes

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